Substituted pyrimidinyloxy pyridine derivatives as herbicides

ABSTRACT

Disclosed are compounds of Formula 1, including all stereoisomers, N-oxides, and salts thereof, 
                         
wherein
         Q, Z, R 2 , R 3  and m are as defined in the disclosure.       

     Also disclosed are compositions containing the compounds of Formula 1 and methods for controlling undesired vegetation comprising contacting the undesired vegetation or its environment with an effective amount of a compound or a composition of the invention.

CROSS-REFERENCE TO RELATED APPLICATIONS

This application is a continuation of International Application No.PCT/US2016/022562, filed on Mar. 16, 2016, which claims priority to U.S.Provisional Application No. 62/134,665, filed on Mar. 18, 2015, both ofwhich are incorporated by reference in their entirety herein.

FIELD OF THE INVENTION

This invention relates to certain substituted pyrimidyloxy pyridinederivatives, their N-oxides, salts and compositions, and methods oftheir use for controlling undesirable vegetation.

BACKGROUND OF THE INVENTION

The control of undesired vegetation is extremely important in achievinghigh crop efficiency. Achievement of selective control of the growth ofweeds especially in such useful crops as rice, soybean, sugar beet,maize, potato, wheat, barley, tomato and plantation crops, among others,is very desirable. Unchecked weed growth in such useful crops can causesignificant reduction in productivity and thereby result in increasedcosts to the consumer. The control of undesired vegetation in noncropareas is also important. Many products are commercially available forthese purposes, but the need continues for new compounds that are moreeffective, less costly, less toxic, environmentally safer or havedifferent sites of action.

SUMMARY OF THE INVENTION

This invention is directed to compounds of Formula 1 (including allstereoisomers), N-oxides, and salts thereof, agricultural compositionscontaining them and their use as herbicides:

-   -   Q is a 5- or 6-membered aromatic heterocylic ring optionally        substituted with 1 to 4 R¹;    -   Z is O or S;    -   each R¹ is independently halogen, cyano, nitro, SF₅, CHO,        C(═O)NH₂, C(═S)NH₂, SO₂NH₂, C₁-C₄ alkyl, C₂-C₄ alkenyl, C₂-C₄        alkynyl, C₁-C₄ haloalkyl, C₂-C₄ haloalkenyl, C₂-C₄ haloalkynyl,        C₃-C₆ cycloalkyl, C₃-C₆ halocycloalkyl, C₄-C₈ alkylcycloalkyl,        C₄-C₈ cycloalkylalkyl, C₂-C₆ alkylcarbonyl, C₂-C₆        haloalkylcarbonyl, C₂-C₆ alkoxycarbonyl, C₃-C₇        cycloalkylcarbonyl, C₂-C₈ alkylaminocarbonyl, C₃-C₁₀        dialkylaminocarbonyl, C₁-C₄ alkoxy, C₃-C₄ alkenyloxy, C₃-C₄        alkynyloxy, C₁-C₄ haloalkoxy, C₃-C₄ haloalkenyloxy, C₃-C₄        haloalkynyloxy, C₃-C₆ cycloalkoxy, C₃-C₆ halocycloalkoxy, C₄-C₈        cycloalkylalkoxy, C₂-C₆ alkoxyalkyl, C₂-C₆ haloalkoxyalkyl,        C₂-C₆ alkoxyhaloalkyl, C₂-C₆ alkoxyalkoxy, C₂-C₄        alkylcarbonyloxy, C₂-C₆ cyanoalkyl, C₂-C₆ cyanoalkoxy, C₁-C₄        hydroxyalkyl, C₂-C₄ alkylthioalkyl, SO_(n)R^(1A), Si(CH₃)₃ or        B(—OC(R^(1B))₂C(R^(1B))₂O—); or a phenyl ring optionally        substituted with up to 5 substituents independently selected        from R^(1C); or a 5- or 6-membered heteroaromatic ring        containing ring members selected from carbon atoms and up to 4        heteroatoms independently selected from up to 2 O, up to 2 S and        up to 4 N atoms, each ring optionally substituted with up to 3        substituents independently selected from R^(1C) on carbon atom        ring members and R^(1D) on nitrogen atom ring members;    -   R² is halogen, cyano, nitro, C₁-C₄ alkoxy, C₁-C₄ alkyl, C₂-C₆        alkenyl, C₂-C₆ alkynyl, SO_(n)R^(2A), C₁-C₄ haloalkyl or C₃-C₆        cycloalkyl;    -   each R³ is independently halogen, cyano, hydroxy, nitro, amino,        CHO, C(═O)NH₂, C(═S)NH₂, SO₂NH₂, C₁-C₄ alkyl, C₂-C₄ alkenyl,        C₂-C₄ alkynyl, C₁-C₄ haloalkyl, C₂-C₄ haloalkenyl, C₂-C₄        haloalkynyl, C₃-C₆ cycloalkyl, C₃-C₆ halocycloalkyl, C₄-C₈        alkylcycloalkyl, C₄-C₈ cycloalkylalkyl, C₂-C₆ alkylcarbonyl,        C₂-C₆ haloalkylcarbonyl, C₂-C₆ alkoxycarbonyl, C₃-C₇        cycloalkylcarbonyl, C₁-C₄ alkoxy, C₃-C₄ alkenyloxy, C₃-C₄        alkynyloxy, C₁-C₄ haloalkoxy, C₃-C₄ haloalkenyloxy, C₃-C₄        haloalkynyloxy, C₃-C₆ cycloalkoxy, C₃-C₆ halocycloalkoxy, C₄-C₈        cycloalkylalkoxy, C₂-C₆ alkoxyalkyl, C₂-C₆ haloalkoxyalkyl,        C₂-C₆ alkoxyhaloalkyl, C₂-C₆ alkoxyalkoxy, C₂-C₄        alkylcarbonyloxy, C₂-C₆ cyanoalkyl, C₂-C₆ cyanoalkoxy, C₂-C₄        alkylthioalkyl, Si(CH₃)₃, C≡CSi(CH₃)₃, C(═O)N(R^(3A))(R^(3B)),        C(═NOR^(3C))H, C(═NR^(3D))H or SO_(n)R^(3E); or a phenyl ring        optionally substituted with up to 5 substituents independently        selected from R^(3F); or a 5- or 6-membered heteroaromatic ring        containing ring members selected from carbon atoms and up to 4        heteroatoms independently selected from up to 2 O, up to 2 S and        up to 4 N atoms, each ring optionally substituted with up to 3        substituents independently selected from R^(3F) on carbon atom        ring members and R^(3G) on nitrogen atom ring members; or        pyrimidinyloxy;    -   m is 0, 1, 2 or 3;    -   each n is independently 0, 1 or 2;    -   each R^(1A), R^(2A) and R^(3E) is independently C₁-C₄ alkyl,        C₁-C₄ haloalkyl, C₁-C₄ alkylamino or C₂-C₆ dialkylamino;    -   each R^(1B) is independently H or C₁-C₄ alkyl;    -   each R^(1C) is independently hydroxy, halogen, cyano, nitro,        C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₁-C₆ alkoxy or C₁-C₆ haloalkoxy;    -   each R^(1D) is independently cyano, C₁-C₆ alkyl, C₁-C₆        haloalkyl, C₁-C₆ alkoxy or C₂-C₆ alkylcarbonyl;    -   each R^(3A) is independently C₁-C₄ alkyl or C₁-C₄ haloalkyl;    -   each R^(3B) is independently H, C₁-C₄ alkyl or C₁-C₄ haloalkyl;    -   each R^(3C) is independently H or C₁-C₄ alkyl;    -   each R^(3D) is independently H, amino, C₁-C₄ alkyl or C₁-C₄        alkylamino;    -   each R^(3F) is independently hydroxy, halogen, cyano, nitro,        C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₁-C₆ alkoxy or C₁-C₆ haloalkoxy;        and    -   each R^(3G) is independently cyano, C₁-C₆ alkyl, C₁-C₆        haloalkyl, C₁-C₆ alkoxy or C₂-C₆ alkylcarbonyl.

More particularly, this invention relates to a compound of Formula 1including all geometric and stereoisomers, an N-oxide or a salt thereof.

This invention also relates to a herbicidal composition comprising aherbicidally effective amount of a compound of the invention and atleast one additional component selected from the group consisting ofsurfactants, solid diluents and liquid diluents.

This invention also relates to a herbicidal composition comprising (a) acompound of the invention and (b) at least one other herbicide (e.g., atleast one other herbicide having the same or different site of action).

This invention further relates to a method for controlling the growth ofundesired vegetation comprising contacting the vegetation or itsenvironment with a herbicidally effective amount of a compound of theinvention (e.g., as a composition described herein).

This invention also includes a herbicidal mixture comprising (a) acompound selected from Formula 1, N-oxides, and salts thereof, and (b)at least one additional active ingredient selected from (b1) through(b16); and salts of compounds of (b1) through (b16), as described below.

DETAILS OF THE INVENTION

As used herein, the terms “comprises,” “comprising,” “includes,”“including,” “has,” “having,” “contains”, “containing,” “characterizedby” or any other variation thereof, are intended to cover anon-exclusive inclusion, subject to any limitation explicitly indicated.For example, a composition, mixture, process, method, article, orapparatus that comprises a list of elements is not necessarily limitedto only those elements but may include other elements not expresslylisted or inherent to such composition, mixture, process, method,article, or apparatus.

The transitional phrase “consisting of” excludes any element, step, oringredient not specified. If in the claim, such would close the claim tothe inclusion of materials other than those recited except forimpurities ordinarily associated therewith. When the phrase “consistingof” appears in a clause of the body of a claim, rather than immediatelyfollowing the preamble, it limits only the element set forth in thatclause; other elements are not excluded from the claim as a whole.

The transitional phrase “consisting essentially of” is used to define acomposition, method or apparatus that includes materials, steps,features, components, or elements, in addition to those literallydisclosed, provided that these additional materials, steps, features,components, or elements do not materially affect the basic and novelcharacteristic(s) of the claimed invention. The term “consistingessentially of” occupies a middle ground between “comprising” and“consisting of”.

Where applicants have defined an invention or a portion thereof with anopen-ended term such as “comprising,” it should be readily understoodthat (unless otherwise stated) the description should be interpreted toalso describe such an invention using the terms “consisting essentiallyof” or “consisting of.”

Further, unless expressly stated to the contrary, “or” refers to aninclusive or and not to an exclusive or. For example, a condition A or Bis satisfied by any one of the following: A is true (or present) and Bis false (or not present), A is false (or not present) and B is true (orpresent), and both A and B are true (or present).

Also, the indefinite articles “a” and “an” preceding an element orcomponent of the invention are intended to be nonrestrictive regardingthe number of instances (i.e. occurrences) of the element or component.Therefore “a” or “an” should be read to include one or at least one, andthe singular word form of the element or component also includes theplural unless the number is obviously meant to be singular.

As referred to herein, the term “seedling”, used either alone or in acombination of words means a young plant developing from the embryo of aseed.

As referred to herein, the term “broadleaf” used either alone or inwords such as “broadleaf weed” means dicot or dicotyledon, a term usedto describe a group of angiosperms characterized by embryos having twocotyledons.

In the above recitations, the term “alkyl”, used either alone or incompound words such as “alkylthio” or “haloalkyl” includesstraight-chain or branched alkyl, such as, methyl, ethyl, n-propyl,i-propyl, or the different butyl, pentyl or hexyl isomers. “Alkenyl”includes straight-chain or branched alkenes such as ethenyl, 1-propenyl,2-propenyl, and the different butenyl, pentenyl and hexenyl isomers.“Alkenyl” also includes polyenes such as 1,2-propadienyl and2,4-hexadienyl. “Alkynyl” includes straight-chain or branched alkynessuch as ethynyl, 1-propynyl, 2-propynyl and the different butynyl,pentynyl and hexynyl isomers. “Alkynyl” can also include moietiescomprised of multiple triple bonds such as 2,5-hexadiynyl. “Alkylene”denotes a straight-chain or branched alkanediyl. Examples of “alkylene”include CH₂, CH₂CH₂, CH(CH₃), CH₂CH₂CH₂, CH₂CH(CH₃) and the differentbutylene isomers. “Alkenylene” denotes a straight-chain or branchedalkenediyl containing one olefinic bond. Examples of “alkenylene”include CH═CH, CH₂CH═CH, CH═C(CH₃) and the different butenylene isomers.“Alkynylene” denotes a straight-chain or branched alkynediyl containingone triple bond. Examples of “alkynylene” include C≡C, CH₂C≡C, C≡CCH₂and the different butynylene isomers.

“Alkoxy” includes, for example, methoxy, ethoxy, n-propyloxy,isopropyloxy and the different butoxy, pentoxy and hexyloxy isomers.“Alkoxyalkyl” denotes alkoxy substitution on alkyl. Examples of“alkoxyalkyl” include CH₃OCH₂, CH₃OCH₂CH₂, CH₃CH₂OCH₂, CH₃CH₂CH₂CH₂OCH₂and CH₃CH₂OCH₂CH₂. “Alkoxyalkoxy” denotes alkoxy substitution on alkoxy.“Alkenyloxy” includes straight-chain or branched alkenyloxy moieties.Examples of “alkenyloxy” include H₂C═CHCH₂O, (CH₃)₂C═CHCH₂O,(CH₃)CH═CHCH₂O, (CH₃)CH═C(CH₃)CH₂O and CH₂═CHCH₂CH₂O. “Alkynyloxy”includes straight-chain or branched alkynyloxy moieties. Examples of“alkynyloxy” include HC≡CCH₂O, CH₃C≡CCH₂O and CH₃C≡CCH₂CH₂O. “Alkylthio”includes branched or straight-chain alkylthio moieties such asmethylthio, ethylthio, and the different propylthio, butylthio,pentylthio and hexylthio isomers. “Alkylsulfinyl” includes bothenantiomers of an alkylsulfinyl group. Examples of “alkylsulfinyl”include CH₃S(O)—, CH₃CH₂S(O)—, CH₃CH₂CH₂S(O)—, (CH₃)₂CHS(O)— and thedifferent butylsulfinyl, pentylsulfinyl and hexylsulfinyl isomers.Examples of “alkylsulfonyl” include CH₃S(O)₂—, CH₃CH₂S(O)₂—,CH₃CH₂CH₂S(O)₂—, (CH₃)₂CHS(O)₂—, and the different butylsulfonyl,pentylsulfonyl and hexylsulfonyl isomers. “Alkylthioalkyl” denotesalkylthio substitution on alkyl. Examples of “alkylthioalkyl” includeCH₃SCH₂, CH₃SCH₂CH₂, CH₃CH₂SCH₂, CH₃CH₂CH₂CH₂SCH₂ and CH₃CH₂SCH₂CH₂.“Cyanoalkyl” denotes an alkyl group substituted with one cyano group.Examples of “cyanoalkyl” include NCCH₂, NCCH₂CH₂ and CH₃CH(CN)CH₂.“Alkylamino”, “dialkylamino”, and the like, are defined analogously tothe above examples.

“Cycloalkyl” includes, for example, cyclopropyl, cyclobutyl, cyclopentyland cyclohexyl. The term “alkylcycloalkyl” denotes alkyl substitution ona cycloalkyl moiety and includes, for example, ethylcyclopropyl,i-propylcyclobutyl, 3-methylcyclopentyl and 4-methylcyclohexyl. The term“cycloalkylalkyl” denotes cycloalkyl substitution on an alkyl moiety.Examples of “cycloalkylalkyl” include cyclopropylmethyl,cyclopentylethyl, and other cycloalkyl moieties bonded to straight-chainor branched alkyl groups. The term “cycloalkoxy” denotes cycloalkyllinked through an oxygen atom such as cyclopentyloxy and cyclohexyloxy.

The term “halogen”, either alone or in compound words such as“haloalkyl”, or when used in descriptions such as “alkyl substitutedwith halogen” includes fluorine, chlorine, bromine or iodine. Further,when used in compound words such as “haloalkyl”, or when used indescriptions such as “alkyl substituted with halogen” said alkyl may bepartially or fully substituted with halogen atoms which may be the sameor different. Examples of “haloalkyl” or “alkyl substituted withhalogen” include F₃C, ClCH₂, CF₃CH₂ and CF₃CCl₂. The terms“halocycloalkyl”, “haloalkoxy”, “haloalkylthio”, “haloalkenyl”,“haloalkynyl”, and the like, are is defined analogously to the term“haloalkyl”. Examples of “haloalkoxy” include CF₃O—, CCl₃CH₂O—,HCF₂CH₂CH₂O— and CF₃CH₂O—. Examples of “haloalkylthio” include CCl₃S—,CF₃S—, CCl₃CH₂S— and ClCH₂CH₂CH₂S—. Examples of “haloalkylsulfinyl”include CF₃S(O)—, CCl₃S(O)—, CF₃CH₂S(O)— and CF₃CF₂S(O)—. Examples of“haloalkylsulfonyl” include CF₃S(O)₂—, CCl₃S(O)₂—, CF₃CH₂S(O)₂— andCF₃CF₂S(O)₂—. Examples of “haloalkenyl” include (Cl)₂C═CHCH₂— andCF₃CH₂CH═CHCH₂—. Examples of “haloalkynyl” include HC≡CCHCl—, CF₃C≡C—,CCl₃C≡C— and FCH₂C≡CCH₂—. Examples of “haloalkoxyalkoxy” includeCF₃OCH₂O—, ClCH₂CH₂OCH₂CH₂O—, Cl₃CCH₂OCH₂O— as well as branched alkylderivatives.

“Alkylcarbonyl” denotes a straight-chain or branched alkyl moietiesbonded to a C(═O) moiety. Examples of “alkylcarbonyl” include CH₃C(═O)—,CH₃CH₂CH₂C(═O)— and (CH₃)₂CHC(═O)—. Examples of “alkoxycarbonyl” includeCH₃OC(═O)—, CH₃CH₂OC(═O)—, CH₃CH₂CH₂OC(═O)—, (CH₃)₂CHOC(═O)— and thedifferent butoxy- or pentoxycarbonyl isomers.

The total number of carbon atoms in a substituent group is indicated bythe “C_(i)-C_(j)” prefix where i and j are numbers from 1 to 10. Forexample, C₁-C₄ alkylsulfonyl designates methylsulfonyl throughbutylsulfonyl; C₂ alkoxyalkyl designates CH₃OCH₂—; C₃ alkoxyalkyldesignates, for example, CH₃CH(OCH₃)—, CH₃OCH₂CH₂— or CH₃CH₂OCH₂—; andC₄ alkoxyalkyl designates the various isomers of an alkyl groupsubstituted with an alkoxy group containing a total of four carbonatoms, examples including CH₃CH₂CH₂OCH₂— and CH₃CH₂OCH₂CH₂—.

When a compound is substituted with a substituent bearing a subscriptthat indicates the number of said substituents can exceed 1, saidsubstituents (when they exceed 1) are independently selected from thegroup of defined substituents, e.g., [(R³)_(m)], m is 0, 1, 2 or 3).Further, when the subscript indicates a range, e.g. (R)_(i-j), then thenumber of substituents may be selected from the integers between i and jinclusive. When a group contains a substituent which can be hydrogen,for example (R¹ or R³), then when this substituent is taken as hydrogen,it is recognized that this is equivalent to said group beingunsubstituted. When a variable group is shown to be optionally attachedto a position, for example [(R³)_(m)] wherein m may be 0, then hydrogenmay be at the position even if not recited in the variable groupdefinition. When one or more positions on a group are said to be “notsubstituted” or “unsubstituted”, then hydrogen atoms are attached totake up any free valency.

Unless otherwise indicated, a “ring” or “ring system” as a component ofFormula 1 (e.g., substituent Q) is heterocyclic. The term “ring system”denotes two or more fused rings. The terms “bicyclic ring system” and“fused bicyclic ring system” denote a ring system consisting of twofused rings, in which either ring can be saturated, partiallyunsaturated, or fully unsaturated unless otherwise indicated. The term“fused heterobicyclic ring system” denotes a fused bicyclic ring systemin which at least one ring atom is not carbon. A “bridged bicyclic ringsystem” is formed by bonding a segment of one or more atoms tononadjacent ring members of a ring. The term “ring member” refers to anatom or other moiety (e.g., C(═O), C(═S), S(O) or S(O)₂) forming thebackbone of a ring or ring system.

The terms “carbocyclic ring”, “carbocycle” or “carbocyclic ring system”denote a ring or ring system wherein the atoms forming the ring backboneare selected only from carbon. Unless otherwise indicated, a carbocyclicring can be a saturated, partially unsaturated, or fully unsaturatedring. When a fully unsaturated carbocyclic ring satisfies Hückel's rule,then said ring is also called an “aromatic ring”. “Saturatedcarbocyclic” refers to a ring having a backbone consisting of carbonatoms linked to one another by single bonds; unless otherwise specified,the remaining carbon valences are occupied by hydrogen atoms.

The terms “heterocyclic ring”, “heterocycle” or “heterocyclic ringsystem” denote a ring or ring system in which at least one atom formingthe ring backbone is not carbon, e.g., nitrogen, oxygen or sulfur.Typically a heterocyclic ring contains no more than 4 nitrogens, no morethan 2 oxygens and no more than 2 sulfurs. Unless otherwise indicated, aheterocyclic ring can be a saturated, partially unsaturated, or fullyunsaturated ring. When a fully unsaturated heterocyclic ring satisfiesHückel's rule, then said ring is also called a “heteroaromatic ring” or“aromatic heterocyclic ring”. Unless otherwise indicated, heterocyclicrings and ring systems can be attached through any available carbon ornitrogen by replacement of a hydrogen on said carbon or nitrogen.

“Aromatic” indicates that each of the ring atoms is essentially in thesame plane and has a p-orbital perpendicular to the ring plane, and that(4n+2) π electrons, where n is a positive integer, are associated withthe ring to comply with Hückel's rule. The term “aromatic ring system”denotes a carbocyclic or heterocyclic ring system in which at least onering of the ring system is aromatic. The term “aromatic carbocyclic ringsystem” denotes a carbocyclic ring system in which at least one ring ofthe ring system is aromatic. The term “aromatic heterocyclic ringsystem” denotes a heterocyclic ring system in which at least one ring ofthe ring system is aromatic. The term “nonaromatic ring system” denotesa carbocyclic or heterocyclic ring system that may be fully saturated,as well as partially or fully unsaturated, provided that none of therings in the ring system are aromatic. The term “nonaromatic carbocyclicring system” in which no ring in the ring system is aromatic. The term“nonaromatic heterocyclic ring system” denotes a heterocyclic ringsystem in which no ring in the ring system is aromatic.

The term “optionally substituted” in connection with the heterocyclicrings refers to groups which are unsubstituted or have at least onenon-hydrogen substituent that does not extinguish the biologicalactivity possessed by the unsubstituted analog. As used herein, thefollowing definitions shall apply unless otherwise indicated. The term“optionally substituted” is used interchangeably with the phrase“substituted or unsubstituted” or with the term “(un)substituted.”Unless otherwise indicated, an optionally substituted group may have asubstituent at each substitutable position of the group, and eachsubstitution is independent of the other.

When Q is a 5- or 6-membered aromatic heterocyclic ring, it may beattached to the remainder of Formula 1 though any available carbon ornitrogen ring atom, unless otherwise described.

R³ can be (among others) phenyl optionally substituted with one or moresubstituents selected from a group of substituents as defined in theSummary of the Invention. An example of phenyl optionally substitutedwith one to five substituents is the ring illustrated as U-1 in Exhibit1, wherein R^(v) is R^(3F) as defined in the Summary of the Inventionfor R³ and r is an integer (from 0 to 5).

As noted above, Q or R³ can be (among others) a 5- or 6-memberedaromatic heterocyclic ring, optionally substituted with one or moresubstituents selected from a group of substituents as defined in theSummary of the Invention. Examples of a 5- or 6-membered aromaticheterocyclic ring optionally substituted with from one or moresubstituents include the rings U-2 through U-61 illustrated in Exhibit 1wherein R^(v) is any substituent as defined in the Summary of theInvention for Q or R³ and r is an integer from 0 to 3, limited by thenumber of available positions on each U group. As U-29, U-30, U-36,U-37, U-38, U-39, U-40, U-41, U-42 and U-43 have only one availableposition, for these U groups r is limited to the integers 0 or 1, and rbeing 0 means that the U group is unsubstituted and a hydrogen ispresent at the position indicated by (R^(v))_(r).

Although R^(v) groups are shown in the structures U-1 through U-61, itis noted that they do not need to be present since they are optionalsubstituents. Note that when R^(v) is H when attached to an atom, thisis the same as if said atom is unsubstituted. The nitrogen atoms thatrequire substitution to fill their valence are substituted with H orR^(v). Note that when the attachment point between (R^(v))_(r) and the Ugroup is illustrated as floating, (R^(v))_(r) can be attached to anyavailable carbon atom or nitrogen atom of the U group. Note that whenthe attachment point on the U group is illustrated as floating, the Ugroup can be attached to the remainder of Formula 1 through anyavailable carbon or nitrogen of the U group by replacement of a hydrogenatom. Note that some U groups can only be substituted with less than 4R^(v) groups (e.g., U-2 through U-5, U-7 through U-48, and U-52 throughU-61).

A wide variety of synthetic methods are known in the art to enablepreparation of aromatic and nonaromatic heterocyclic rings and ringsystems; for extensive reviews see the eight volume set of ComprehensiveHeterocyclic Chemistry, A. R. Katritzky and C. W. Rees editors-in-chief,Pergamon Press, Oxford, 1984 and the twelve volume set of ComprehensiveHeterocyclic Chemistry II, A. R. Katritzky, C. W. Rees and E. F. V.Scriven editors-in-chief, Pergamon Press, Oxford, 1996.

Compounds of this invention can exist as one or more stereoisomers. Thevarious stereoisomers include enantiomers, diastereomers, atropisomersand geometric isomers. Stereoisomers are isomers of identicalconstitution but differing in the arrangement of their atoms in spaceand include enantiomers, diastereomers, cis-trans isomers (also known asgeometric isomers) and atropisomers. Atropisomers result from restrictedrotation about single bonds where the rotational barrier is high enoughto permit isolation of the isomeric species. One skilled in the art willappreciate that one stereoisomer may be more active and/or may exhibitbeneficial effects when enriched relative to the other stereoisomer(s)or when separated from the other stereoisomer(s). Additionally, theskilled artisan knows how to separate, enrich, and/or to selectivelyprepare said stereoisomers. The compounds of the invention may bepresent as a mixture of stereoisomers, individual stereoisomers or as anoptically active form.

Compounds of Formula 1 typically exist in more than one form, andFormula 1 thus include all crystalline and non-crystalline forms of thecompounds they represent. Non-crystalline forms include embodimentswhich are solids such as waxes and gums as well as embodiments which areliquids such as solutions and melts. Crystalline forms includeembodiments which represent essentially a single crystal type andembodiments which represent a mixture of polymorphs (i.e. differentcrystalline types). The term “polymorph” refers to a particularcrystalline form of a chemical compound that can crystallize indifferent crystalline forms, these forms having different arrangementsand/or conformations of the molecules in the crystal lattice. Althoughpolymorphs can have the same chemical composition, they can also differin composition due the presence or absence of co-crystallized water orother molecules, which can be weakly or strongly bound in the lattice.Polymorphs can differ in such chemical, physical and biologicalproperties as crystal shape, density, hardness, color, chemicalstability, melting point, hygroscopicity, suspensibility, dissolutionrate and biological availability. One skilled in the art will appreciatethat a polymorph of a compound of Formula 1 can exhibit beneficialeffects (e.g., suitability for preparation of useful formulations,improved biological performance) relative to another polymorph or amixture of polymorphs of the same compound of Formula 1. Preparation andisolation of a particular polymorph of a compound of Formula 1 can beachieved by methods known to those skilled in the art including, forexample, crystallization using selected solvents and temperatures. For acomprehensive discussion of polymorphism see R. Hilfiker, Ed.,Polymorphism in the Pharmaceutical Industry, Wiley-VCH, Weinheim, 2006.

One skilled in the art will appreciate that not all nitrogen-containingheterocycles can form N-oxides since the nitrogen requires an availablelone pair for oxidation to the oxide; one skilled in the art willrecognize those nitrogen-containing heterocycles which can formN-oxides. One skilled in the art will also recognize that tertiaryamines can form N-oxides. Synthetic methods for the preparation ofN-oxides of heterocycles and tertiary amines are very well known by oneskilled in the art including the oxidation of heterocycles and tertiaryamines with peroxy acids such as peracetic and m-chloroperbenzoic acid(MCPBA), hydrogen peroxide, alkyl hydroperoxides such as t-butylhydroperoxide, sodium perborate, and dioxiranes such asdimethyldioxirane. These methods for the preparation of N-oxides havebeen extensively described and reviewed in the literature, see forexample: T. L. Gilchrist in Comprehensive Organic Synthesis, vol. 7, pp748-750, S. V. Ley, Ed., Pergamon Press; M. Tisler and B. Stanovnik inComprehensive Heterocyclic Chemistry, vol. 3, pp 18-20, A. J. Boultonand A. McKillop, Eds., Pergamon Press; M. R. Grimmett and B. R. T. Keenein Advances in Heterocyclic Chemistry, vol. 43, pp 149-161, A. R.Katritzky, Ed., Academic Press; M. Tisler and B. Stanovnik in Advancesin Heterocyclic Chemistry, vol. 9, pp 285-291, A. R. Katritzky and A. J.Boulton, Eds., Academic Press; and G. W. H. Cheeseman and E. S. G.Werstiuk in Advances in Heterocyclic Chemistry, vol. 22, pp 390-392, A.R. Katritzky and A. J. Boulton, Eds., Academic Press.

One skilled in the art recognizes that because in the environment andunder physiological conditions salts of chemical compounds are inequilibrium with their corresponding nonsalt forms, salts share thebiological utility of the nonsalt forms. Thus a wide variety of salts ofa compound of Formula 1 are useful for control of undesired vegetation(i.e. are agriculturally suitable). The salts of a compound of Formula 1include acid-addition salts with inorganic or organic acids such ashydrobromic, hydrochloric, nitric, phosphoric, sulfuric, acetic,butyric, fumaric, lactic, maleic, malonic, oxalic, propionic, salicylic,tartaric, 4-toluenesulfonic or valeric acids. When a compound of Formula1 contains an acidic moiety such as a carboxylic acid or phenol, saltsalso include those formed with organic or inorganic bases such aspyridine, triethylamine or ammonia, or amides, hydrides, hydroxides orcarbonates of sodium, potassium, lithium, calcium, magnesium or barium.Accordingly, the present invention comprises compounds selected fromFormula 1, N-oxides and agriculturally suitable salts thereof.

Embodiments of the present invention as described in the Summary of theInvention include (where Formula 1 as used in the following Embodimentsincludes N-oxides and salts thereof):

Embodiment 1

-   -   A compound of Formula 1 wherein Q is selected from

-   -   r is 0, 1, 2 or 3; and s is 0 or 1.

Embodiment 2

-   -   A compound of Embodiment 1 wherein Q is selected from Q-1        through Q-51.

Embodiment 3

-   -   A compound of Embodiment 2 wherein Q is selected from Q-8        through Q-27 and Q-46.

Embodiment 3a

-   -   A compound of Embodiment 3 wherein Q is selected from Q-18,        Q-20, Q-27 and Q-46.

Embodiment 3b

-   -   A compound of Embodiment 2 wherein Q is selected from Q-12        through Q-27.

Embodiment 3c

-   -   A compound of Embodiment 2 wherein Q is selected from Q-12        through Q-27 and Q-46.

Embodiment 3d

-   -   A compound of Embodiment 1 wherein Q is selected from

Embodiment 4

-   -   A compound of Embodiment 3a wherein Q is selected from

Embodiment 5

-   -   A compound of Embodiment 4 wherein Q is Q-18.

Embodiment 6

-   -   A compound of Embodiment 4 wherein Q is Q-20.

Embodiment 7

-   -   A compound of Embodiment 4 wherein Q is Q-27.

Embodiment 7a

-   -   A compound of Embodiment 3 wherein Q is selected from Q-18, Q-19        and Q-20.

Embodiment 7b

-   -   A compound of Embodiment 1 wherein Q is Q-52.

Embodiment 7c

-   -   A compound of Embodiment 1 wherein Q is other than Q-8, Q-9 and        Q-10.

Embodiment 8

-   -   A compound of Formula 1 or any one of Embodiments 1 through 7        either alone or in combination, wherein Z is O.

Embodiment 9

-   -   A compound of Formula 1 or any one of Embodiments 1 through 8        either alone or in combination, wherein each R¹ is independently        halogen, cyano, SF₅, CHO, C₁-C₄ alkyl, C₂-C₄ alkenyl, C₂-C₄        alkynyl, C₁-C₄ haloalkyl, C₂-C₄ haloalkenyl, C₂-C₄ haloalkynyl,        C₂-C₆ alkylcarbonyl, C₂-C₆ haloalkylcarbonyl, C₂-C₆        alkoxycarbonyl, C₁-C₄ alkoxy, C₃-C₄ alkenyloxy, C₃-C₄        alkynyloxy, C₁-C₄ haloalkoxy, C₃-C₄ haloalkenyloxy, C₃-C₄        haloalkynyloxy, C₂-C₆ alkoxyalkyl, C₂-C₆ haloalkoxyalkyl, C₂-C₆        cyanoalkyl, C₁-C₄ hydroxyalkyl, C₂-C₄ alkylthioalkyl or        SO_(n)R^(1A).

Embodiment 10

-   -   A compound of Embodiment 9 wherein each R¹ is independently        halogen, cyano, CHO, C₁-C₄ alkyl, C₂-C₄ alkenyl, C₂-C₄ alkynyl,        C₁-C₄ haloalkyl, C₂-C₄ haloalkenyl, C₂-C₄ haloalkynyl, C₁-C₄        alkoxy, C₃-C₄ alkenyloxy, C₃-C₄ alkynyloxy, C₁-C₄ haloalkoxy,        C₃-C₄ haloalkenyloxy, C₃-C₄ haloalkynyloxy, C₂-C₆ alkoxyalkyl,        C₂-C₆ haloalkoxyalkyl, C₁-C₄ hydroxyalkyl, C₂-C₄ alkylthioalkyl        or SO_(n)R^(1A).

Embodiment 11

-   -   A compound of Embodiment 10 wherein each R¹ is independently        halogen, cyano, C₁-C₄ alkyl, C₁-C₄ haloalkyl, C₁-C₄ alkoxy,        C₁-C₄ haloalkoxy or SO_(n)R^(1A).

Embodiment 12

-   -   A compound of Embodiment 11 wherein each R¹ is independently        halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl or C₁-C₄ haloalkoxy.

Embodiment 13

-   -   A compound of Embodiment 12 wherein each R¹ is independently        halogen, C₁-C₄ haloalkyl or C₁-C₄ haloalkoxy.

Embodiment 14

-   -   A compound of Embodiment 13 wherein each R¹ is independently        halogen or C₁-C₄ haloalkyl.

Embodiment 15

-   -   A compound of Embodiment 14 wherein each R¹ is independently F,        Cl, Br, CF₃, CHF₂ or CH₂F.

Embodiment 16

-   -   A compound of Formula 1 or any one of Embodiments 1 through 15        either alone or in combination, wherein r is 0, 1 or 2.

Embodiment 17

-   -   A compound of Embodiment 16 wherein r is 1.

Embodiment 18

-   -   A compound of Formula 1 or any one of Embodiments 1 through 15        either alone or in combination, wherein s is 1.

Embodiment 19

-   -   A compound of Formula 1 or any one of Embodiments 1 through 18        either alone or in combination, wherein when Q is Q-18 and r is        1 then R¹ is attached at the 5 position of the Q-18 ring.

Embodiment 20

-   -   A compound of Formula 1 or any one of Embodiments 1 through 18        either alone or in combination, wherein when Q is Q-20 and r is        1 then R¹ is attached at the 3 position of the Q-20 ring.

Embodiment 21

-   -   A compound of Formula 1 or any one of Embodiments 1 through 18        either alone or in combination, wherein when Q is Q-27 and r is        1 then R¹ is attached at the 4 position of the Q-27 ring.

Embodiment 22

-   -   A compound of Formula 1 or any one of Embodiments 1 through 21        either alone or in combination, wherein R² is halogen, C₁-C₄        alkyl or C₁-C₄ haloalkyl.

Embodiment 23

-   -   A compound of Embodiment 22 wherein R² is halogen or C₁-C₄        alkyl.

Embodiment 24

-   -   A compound of Embodiment 23 wherein R² is halogen or CH₃.

Embodiment 25

-   -   A compound of Embodiment 24 wherein R² is halogen.

Embodiment 26

-   -   A compound of Embodiment 25 wherein R² is F, Cl or Br.

Embodiment 27

-   -   A compound of Formula 1 or any one of Embodiments 1 through 26        either alone or in combination, wherein m is 0, 1 or 2.

Embodiment 28

-   -   A compound of Embodiment 27 wherein m is 0 or 1.

Embodiment 29

-   -   A compound of Embodiment 28 wherein m is 1.

Embodiment 30

-   -   A compound of Embodiment 27 wherein m is 0 (i.e. the 4-, 5- and        6-positions are unsubtituted by R³).

Embodiment 31

-   -   A compound of Formula 1 or any one of Embodiments 1 through 30        either alone or in combination, wherein each R³ is independently        halogen, cyano, CHO, C₁-C₄ alkyl, C₂-C₄ alkenyl, C₂-C₄ alkynyl,        C₁-C₄ haloalkyl, C₂-C₄ haloalkenyl, C₂-C₄ haloalkynyl, C₃-C₆        cycloalkyl, C₃-C₆ halocycloalkyl, C₄-C₈ alkylcycloalkyl, C₂-C₆        alkylcarbonyl, C₂-C₆ haloalkylcarbonyl, C₂-C₆ alkoxycarbonyl,        C₁-C₄ alkoxy, C₃-C₄ alkenyloxy, C₃-C₄ alkynyloxy, C₁-C₄        haloalkoxy, C₃-C₄ haloalkenyloxy, C₃-C₄ haloalkynyloxy, C₃-C₆        cycloalkoxy, C₃-C₆ halocycloalkoxy, C₂-C₆ alkoxyalkyl, C₂-C₆        haloalkoxyalkyl, C₂-C₄ alkylcarbonyloxy, C₂-C₆ cyanoalkyl,        C(═O)N(R^(3A))(R^(3B)), C(═NOR^(3C))H or SO_(n)R^(3E); or a        phenyl ring optionally substituted with up to 5 substituents        independently selected from R^(3F); or a 5- or 6-membered        heteroaromatic ring containing ring members selected from carbon        atoms and up to 4 heteroatoms independently selected from up to        2 O, up to 2 S and up to 4 N atoms, each ring optionally        substituted with up to 3 substituents independently selected        from R^(3F) on carbon atom ring members and R^(3G) on nitrogen        atom ring members.

Embodiment 32

-   -   A compound of Embodiment 31 wherein each R³ is independently        halogen, cyano, CHO, C₁-C₄ alkyl, C₂-C₄ alkenyl, C₂-C₄ alkynyl,        C₁-C₄ haloalkyl, C₂-C₄ haloalkenyl, C₂-C₄ haloalkynyl, C₃-C₆        cycloalkyl, C₃-C₆ halocycloalkyl, C₂-C₆ alkylcarbonyl, C₂-C₆        haloalkylcarbonyl, C₂-C₆ alkoxycarbonyl, C₁-C₄ alkoxy, C₁-C₄        haloalkoxy, C₂-C₆ alkoxyalkyl, C₂-C₆ haloalkoxyalkyl, C₂-C₆        cyanoalkyl or SO_(n)R^(3E); or a 5- or 6-membered heteroaromatic        ring containing ring members selected from carbon atoms and up        to 4 heteroatoms independently selected from up to 2 O, up to 2        S and up to 4 N atoms, each ring optionally substituted with up        to 3 substituents independently selected from R^(3F) on carbon        atom ring members and R^(3G) on nitrogen atom ring members.

Embodiment 33

-   -   A compound of Embodiment 32 wherein each R³ is independently        halogen, cyano, C₁-C₄ alkyl, C₂-C₄ alkenyl, C₂-C₄ alkynyl, C₁-C₄        haloalkyl, C₂-C₆ alkylcarbonyl, C₂-C₆ haloalkylcarbonyl, C₂-C₆        alkoxycarbonyl, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₂-C₆        alkoxyalkyl or C₂-C₆ haloalkoxyalkyl.

Embodiment 34

-   -   A compound of Embodiment 33 wherein each R³ is independently        halogen, cyano, C₁-C₄ alkyl or C₁-C₄ haloalkyl.

Embodiment 35

-   -   A compound of Embodiment 34 wherein each R³ is independently        halogen or cyano.

Embodiment 36

-   -   A compound of Embodiment 35 wherein each R³ is independently        halogen.

Embodiment 37

-   -   A compound of Formula 1 or any one of Embodiments 1 through 36        either alone or in combination, wherein each R^(1A) is        independently C₁-C₄ alkyl or C₁-C₄ haloalkyl.

Embodiment 38

-   -   A compound of Embodiment 37 wherein each R^(1A) is independently        C₁-C₄ haloalkyl.

Embodiment 39

-   -   A compound of Formula 1 or any one of Embodiments 1 through 38        either alone or in combination, wherein each R^(3E) is        independently C₁-C₄ alkyl.

Embodiment 39a

-   -   A compound of Formula 1 or any one of Embodiments 1 through 39        either alone or in combination, wherein each R^(3E) is CH₃.

Embodiment 40

-   -   A compound of Formula 1 or any one of Embodiments 1 through 39        either alone or in combination, wherein each R^(3A) is        independently C₁-C₄ alkyl.

Embodiment 41

-   -   A compound of Formula 1 or any one of Embodiments 1 through 40        either alone or in combination, wherein each R^(3B) is        independently H or C₁-C₄ alkyl.

Embodiment 42

-   -   A compound of Formula 1 or any one of Embodiments 1 through 41        either alone or in combination, wherein each R^(3C) is        independently H or C₁-C₄ alkyl.

Embodiment 43

-   -   A compound of Formula 1 or any one of Embodiments 1 through 42        either alone or in combination, wherein each R^(3D) is        independently H or C₁-C₄ alkyl.

Embodiment 44

-   -   A compound of Formula 1 or any one of Embodiments 1 through 43        either alone or in combination, wherein each n is independently        0 or 2.

Embodiment 45

-   -   A compound of Embodiment 44 wherein n is 2.

Embodiment 46

-   -   A compound of Embodiment 44 wherein n is 0.        Embodiments of this invention, including Embodiments 1-46 above        as well as any other embodiments described herein, can be        combined in any manner, and the descriptions of variables in the        embodiments pertain not only to the compounds of Formula 1 but        also to the starting compounds and intermediate compounds useful        for preparing the compounds of Formula 1. In addition,        embodiments of this invention, including Embodiments 1-46 above        as well as any other embodiments described herein, and any        combination thereof, pertain to the compositions and methods of        the present invention.

Combinations of Embodiments 1-46 are illustrated by:

Embodiment A

A compound of Formula 1 wherein

-   -   Q is selected from Q-1 through Q-64;    -   r is 0, 1, 2 or 3;    -   s is 0 or 1;    -   each R¹ is independently halogen, cyano, SF₅, CHO, C₁-C₄ alkyl,        C₂-C₄ alkenyl, C₂-C₄ alkynyl, C₁-C₄ haloalkyl, C₂-C₄        haloalkenyl, C₂-C₄ haloalkynyl, C₂-C₆ alkylcarbonyl, C₂-C₆        haloalkylcarbonyl, C₂-C₆ alkoxycarbonyl, C₁-C₄ alkoxy, C₃-C₄        alkenyloxy, C₃-C₄ alkynyloxy, C₁-C₄ haloalkoxy, C₃-C₄        haloalkenyloxy, C₃-C₄ haloalkynyloxy, C₂-C₆ alkoxyalkyl, C₂-C₆        haloalkoxyalkyl, C₂-C₆ cyanoalkyl, C₁-C₄ hydroxyalkyl, C₂-C₄        alkylthioalkyl or SO_(n)R^(1A);    -   R³ is independently halogen, cyano, CHO, C₁-C₄ alkyl, C₂-C₄        alkenyl, C₂-C₄ alkynyl, C₁-C₄ haloalkyl, C₂-C₄ haloalkenyl,        C₂-C₄ haloalkynyl, C₃-C₆ cycloalkyl, C₃-C₆ halocycloalkyl, C₄-C₈        alkylcycloalkyl, C₂-C₆ alkylcarbonyl, C₂-C₆ haloalkylcarbonyl,        C₂-C₆ alkoxycarbonyl, C₁-C₄ alkoxy, C₃-C₄ alkenyloxy, C₃-C₄        alkynyloxy, C₁-C₄ haloalkoxy, C₃-C₄ haloalkenyloxy, C₃-C₄        haloalkynyloxy, C₃-C₆ cycloalkoxy, C₃-C₆ halocycloalkoxy, C₂-C₆        alkoxyalkyl, C₂-C₆ haloalkoxyalkyl, C₂-C₄ alkylcarbonyloxy,        C₂-C₆ cyanoalkyl, C(═O)N(R^(3A))(R^(3B)), C(═NOR^(3C))H or        SO_(n)R^(3E); or a phenyl ring optionally substituted with up to        5 substituents independently selected from R^(3F); or a 5- or        6-membered heteroaromatic ring containing ring members selected        from carbon atoms and up to 4 heteroatoms independently selected        from up to 2 O, up to 2 S and up to 4 N atoms, each ring        optionally substituted with up to 3 substituents independently        selected from R^(3F) on carbon atom ring members and R^(3G) on        nitrogen atom ring members;    -   Z is O; and    -   m is 0, 1 or 2.

Embodiment B

A compound of Embodiment A wherein

-   -   each R¹ is independently halogen, cyano, CHO, C₁-C₄ alkyl, C₂-C₄        alkenyl, C₂-C₄ alkynyl, C₁-C₄ haloalkyl, C₂-C₄ haloalkenyl,        C₂-C₄ haloalkynyl, C₁-C₄ alkoxy, C₃-C₄ alkenyloxy, C₃-C₄        alkynyloxy, C₁-C₄ haloalkoxy, C₃-C₄ haloalkenyloxy, C₃-C₄        haloalkynyloxy, C₂-C₆ alkoxyalkyl, C₂-C₆ haloalkoxyalkyl, C₁-C₄        hydroxyalkyl, C₂-C₄ alkylthioalkyl or SO_(n)R^(1A);    -   R² is halogen, C₁-C₄ alkyl or C₁-C₄ haloalkyl;    -   each R³ is independently halogen, cyano, CHO, C₁-C₄ alkyl, C₂-C₄        alkenyl, C₂-C₄ alkynyl, C₁-C₄ haloalkyl, C₂-C₄ haloalkenyl,        C₂-C₄ haloalkynyl, C₃-C₆ cycloalkyl, C₃-C₆ halocycloalkyl, C₂-C₆        alkylcarbonyl, C₂-C₆ haloalkylcarbonyl, C₂-C₆ alkoxycarbonyl,        C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₂-C₆ alkoxyalkyl, C₂-C₆        haloalkoxyalkyl, C₂-C₆ cyanoalkyl or SO_(n)R^(3E); or a 5- or        6-membered heteroaromatic ring containing ring members selected        from carbon atoms and up to 4 heteroatoms independently selected        from up to 2 O, up to 2 S and up to 4 N atoms, each ring        optionally substituted with up to 3 substituents independently        selected from R^(3F) on carbon atom ring members and R^(3G) on        nitrogen atom ring members; and    -   m is 0 or 1.

Embodiment B1

A compound of Embodiment A wherein

-   -   Q is selected from Q-12 through Q-27;    -   each R¹ is independently halogen, cyano, CHO, C₁-C₄ alkyl, C₂-C₄        alkenyl, C₂-C₄ alkynyl, C₁-C₄ haloalkyl, C₂-C₄ haloalkenyl,        C₂-C₄ haloalkynyl, C₁-C₄ alkoxy, C₃-C₄ alkenyloxy, C₃-C₄        alkynyloxy, C₁-C₄ haloalkoxy, C₃-C₄ haloalkenyloxy, C₃-C₄        haloalkynyloxy, C₂-C₆ alkoxyalkyl, C₂-C₆ haloalkoxyalkyl, C₁-C₄        hydroxyalkyl, C₂-C₄ alkylthioalkyl or SO_(n)R^(1A);    -   R² is halogen, C₁-C₄ alkyl or C₁-C₄ haloalkyl;    -   each R³ is independently halogen, cyano, CHO, C₁-C₄ alkyl, C₂-C₄        alkenyl, C₂-C₄ alkynyl, C₁-C₄ haloalkyl, C₂-C₄ haloalkenyl,        C₂-C₄ haloalkynyl, C₃-C₆ cycloalkyl, C₃-C₆ halocycloalkyl, C₂-C₆        alkylcarbonyl, C₂-C₆ haloalkylcarbonyl, C₂-C₆ alkoxycarbonyl,        C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₂-C₆ alkoxyalkyl, C₂-C₆        haloalkoxyalkyl, C₂-C₆ cyanoalkyl or SO_(n)R^(3E); or a 5- or        6-membered heteroaromatic ring containing ring members selected        from carbon atoms and up to 4 heteroatoms independently selected        from up to 2 O, up to 2 S and up to 4 N atoms, each ring        optionally substituted with up to 3 substituents independently        selected from R^(3F) on carbon atom ring members and R^(3G) on        nitrogen atom ring members; and    -   m is 0 or 1.

Embodiment C

A compound of Embodiment B wherein

-   -   Q is selected from Q-8 through Q-27 and Q-46;    -   each R¹ is independently halogen, cyano, C₁-C₄ alkyl, C₁-C₄        haloalkyl, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy or SO_(n)R^(1A);    -   R² is halogen or C₁-C₄ alkyl;    -   each R³ is independently halogen, cyano, C₁-C₄ alkyl, C₂-C₄        alkenyl, C₂-C₄ alkynyl, C₁-C₄ haloalkyl, C₂-C₆ alkylcarbonyl,        C₂-C₆ haloalkylcarbonyl, C₂-C₆ alkoxycarbonyl, C₁-C₄ alkoxy,        C₁-C₄ haloalkoxy, C₂-C₆ alkoxyalkyl or C₂-C₆ haloalkoxyalkyl;        and    -   each R^(1A) is independently C₁-C₄ alkyl or C₁-C₄ haloalkyl.

Embodiment C1

A compound of Embodiment B wherein

-   -   Q is selected from

-   -   r is 1;    -   R¹ is independently halogen, cyano, C₁-C₄ alkyl, C₁-C₄        haloalkyl, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy or SO_(n)R^(1A);    -   R² is halogen or C₁-C₄ alkyl;    -   each R³ is independently halogen, cyano, C₁-C₄ alkyl, C₂-C₄        alkenyl, C₂-C₄ alkynyl, C₁-C₄ haloalkyl, C₂-C₆ alkylcarbonyl,        C₂-C₆ haloalkylcarbonyl, C₂-C₆ alkoxycarbonyl, C₁-C₄ alkoxy,        C₁-C₄ haloalkoxy, C₂-C₆ alkoxyalkyl or C₂-C₆ haloalkoxyalkyl;    -   each R^(1A) is independently C₁-C₄ alkyl or C₁-C₄ haloalkyl; and    -   m is 0 or 1.

Embodiment D

A compound of Embodiment C wherein

-   -   Q is selected from Q-18, Q-20 and Q-27;    -   each R¹ is independently halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl        or C₁-C₄ haloalkoxy;    -   R² is halogen or CH₃; and    -   each R³ is independently halogen, cyano, C₁-C₄ alkyl or C₁-C₄        haloalkyl.

Specific embodiments include compounds of Formula 1 selected from thegroup consisting of:

-   2-[[2-(4-bromo-1H-pyrazol-1-yl)-3-pyridinyl]oxy]-5-chloropyrimidine    (Compound 1),-   5-chloro-2-[[2-(4-chloro-1H-pyrazol-1-yl)-3-pyridinyl]oxy]pyrimidine    (Compound 2),-   5-chloro-2-[[2-[3-(difluoromethyl)-5-isoxazolyl]-3-pyridinyl]oxy]pyrimidine    (Compound 5) and-   5-chloro-2-[[2-[5-(difluoromethyl)-3-isoxazolyl]-3-pyridinyl]oxy]pyrimidine    (Compound 6).

This invention also relates to a method for controlling undesiredvegetation comprising applying to the locus of the vegetationherbicidally effective amounts of the compounds of the invention (e.g.,as a composition described herein). Of note as embodiments relating tomethods of use are those involving the compounds of embodimentsdescribed above. Compounds of the invention are particularly useful forselective control of weeds in crops such as wheat, barley, maize,soybean, sunflower, cotton, oilseed rape and rice, and specialty cropssuch as sugarcane, citrus, fruit and nut crops.

Also noteworthy as embodiments are herbicidal compositions of thepresent invention comprising the compounds of embodiments describedabove.

This invention also includes a herbicidal mixture comprising (a) acompound selected from Formula 1, N-oxides, and salts thereof, and (b)at least one additional active ingredient selected from (b1) photosystemII inhibitors, (b2) acetohydroxy acid synthase (AHAS) inhibitors, (b3)acetyl-CoA carboxylase (ACCase) inhibitors, (b4) auxin mimics, (b5)5-enol-pyruvylshikimate-3-phosphate (EPSP) synthase inhibitors, (b6)photosystem I electron diverters, (b7) protoporphyrinogen oxidase (PPO)inhibitors, (b8) glutamine synthetase (GS) inhibitors, (b9) very longchain fatty acid (VLCFA) elongase inhibitors, (b10) auxin transportinhibitors, (b11) phytoene desaturase (PDS) inhibitors, (b12)4-hydroxyphenyl-pyruvate dioxygenase (HPPD) inhibitors, (b13)homogentisate solenesyltransererase (HST) inhibitors, (b14) cellulosebiosynthesis inhibitors, (b15) other herbicides including mitoticdisruptors, organic arsenicals, asulam, bromobutide, cinmethylin,cumyluron, dazomet, difenzoquat, dymron, etobenzanid, flurenol,fosamine, fosamine-ammonium, hydantocidin, metam, methyldymron, oleicacid, oxaziclomefone, pelargonic acid and pyributicarb, and (b16)herbicide safeners; and salts of compounds of (b1) through (b16).

“Photosystem II inhibitors” (b1) are chemical compounds that bind to theD-1 protein at the Q_(B)-binding niche and thus block electron transportfrom Q_(A) to Q_(B) in the chloroplast thylakoid membranes. Theelectrons blocked from passing through photosystem II are transferredthrough a series of reactions to form toxic compounds that disrupt cellmembranes and cause chloroplast swelling, membrane leakage, andultimately cellular destruction. The Q_(B)-binding niche has threedifferent binding sites: binding site A binds the triazines such asatrazine, triazinones such as hexazinone, and uracils such as bromacil,binding site B binds the phenylureas such as diuron, and binding site Cbinds benzothiadiazoles such as bentazon, nitriles such as bromoxyniland phenyl-pyridazines such as pyridate. Examples of photosystem IIinhibitors include ametryn, amicarbazone, atrazine, bentazon, bromacil,bromofenoxim, bromoxynil, chlorbromuron, chloridazon, chlorotoluron,chloroxuron, cumyluron, cyanazine, daimuron, desmedipham, desmetryn,dimefuron, dimethametryn, diuron, ethidimuron, fenuron, fluometuron,hexazinone, ioxynil, isoproturon, isouron, lenacil, linuron, metamitron,methabenzthiazuron, metobromuron, metoxuron, metribuzin, monolinuron,neburon, pentanochlor, phenmedipham, prometon, prometryn, propanil,propazine, pyridafol, pyridate, siduron, simazine, simetryn,tebuthiuron, terbacil, terbumeton, terbuthylazine, terbutryn andtrietazine.

“AHAS inhibitors” (b2) are chemical compounds that inhibit acetohydroxyacid synthase (AHAS), also known as acetolactate synthase (ALS), andthus kill plants by inhibiting the production of the branched-chainaliphatic amino acids such as valine, leucine and isoleucine, which arerequired for protein synthesis and cell growth. Examples of AHASinhibitors include amidosulfuron, azimsulfuron, bensulfuron-methyl,bispyribac-sodium, cloransulam-methyl, chlorimuron-ethyl, chlorsulfuron,cinosulfuron, cyclosulfamuron, diclosulam, ethametsulfuron-methyl,ethoxysulfuron, flazasulfuron, florasulam, flucarbazone-sodium,flumetsulam, flupyrsulfuron-methyl, flupyrsulfuron-sodium,foramsulfuron, halosulfuron-methyl, imazamethabenz-methyl, imazamox,imazapic, imazapyr, imazaquin, imazethapyr, imazosulfuron,iodosulfuron-methyl (including sodium salt), iofensulfuron(2-iodo-N-[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)amino]carbonyl]benzenesulfonamide),mesosulfuron-methyl, metazosulfuron(3-chloro-4-(5,6-dihydro-5-methyl-1,4,2-dioxazin-3-yl)-N-[[(4,6-dimethoxy-2-pyrimidinyl)amino]carbonyl]-1-methyl-1H-pyrazole-5-sulfonamide),metosulam, metsulfuron-methyl, nicosulfuron, oxasulfuron, penoxsulam,primisulfuron-methyl, propoxycarbazone-sodium, propyrisulfuron(2-chloro-N-[[(4,6-dimethoxy-2-pyrimidinyl)amino]carbonyl]-6-propylimidazo[1,2-b]pyridazine-3-sulfonamide),prosulfuron, pyrazosulfuron-ethyl, pyribenzoxim, pyriftalid,pyriminobac-methyl, pyrithiobac-sodium, rimsulfuron,sulfometuron-methyl, sulfosulfuron, thiencarbazone,thifensulfuron-methyl, triafamone(N-[2-[(4,6-dimethoxy-1,3,5-triazin-2-yl)carbonyl]-6-fluorophenyl]-1,1-difluoro-N-methylmethanesulfonamide),triasulfuron, tribenuron-methyl, trifloxysulfuron (including sodiumsalt), triflusulfuron-methyl and tritosulfuron.

“ACCase inhibitors” (b3) are chemical compounds that inhibit theacetyl-CoA carboxylase enzyme, which is responsible for catalyzing anearly step in lipid and fatty acid synthesis in plants. Lipids areessential components of cell membranes, and without them, new cellscannot be produced. The inhibition of acetyl CoA carboxylase and thesubsequent lack of lipid production leads to losses in cell membraneintegrity, especially in regions of active growth such as meristems.Eventually shoot and rhizome growth ceases, and shoot meristems andrhizome buds begin to die back. Examples of ACCase inhibitors includealloxydim, butroxydim, clethodim, clodinafop, cycloxydim, cyhalofop,diclofop, fenoxaprop, fluazifop, haloxyfop, pinoxaden, profoxydim,propaquizafop, quizalofop, sethoxydim, tepraloxydim and tralkoxydim,including resolved forms such as fenoxaprop-P, fluazifop-P, haloxyfop-Pand quizalofop-P and ester forms such as clodinafop-propargyl,cyhalofop-butyl, diclofop-methyl and fenoxaprop-P-ethyl.

Auxin is a plant hormone that regulates growth in many plant tissues.“Auxin mimics” (b4) are chemical compounds mimicking the plant growthhormone auxin, thus causing uncontrolled and disorganized growth leadingto plant death in susceptible species. Examples of auxin mimics includeaminocyclopyrachlor(6-amino-5-chloro-2-cyclopropyl-4-pyrimidinecarboxylic acid) and itsmethyl and ethyl esters and its sodium and potassium salts,aminopyralid, benazolin-ethyl, chloramben, clacyfos, clomeprop,clopyralid, dicamba, 2,4-D, 2,4-DB, dichlorprop, fluroxypyr, halauxifen(4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-2-pyridinecarboxylicacid), halauxifen-methyl (methyl4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-2-pyridinecarboxylate),MCPA, MCPB, mecoprop, picloram, quinclorac, quinmerac, 2,3,6-TBA,triclopyr, and methyl4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-5-fluoro-2-pyridinecarboxylate.

“EPSP synthase inhibitors” (b5) are chemical compounds that inhibit theenzyme, 5-enol-pyruvylshikimate-3-phosphate synthase, which is involvedin the synthesis of aromatic amino acids such as tyrosine, tryptophanand phenylalanine. EPSP inhibitor herbicides are readily absorbedthrough plant foliage and translocated in the phloem to the growingpoints. Glyphosate is a relatively nonselective postemergence herbicidethat belongs to this group. Glyphosate includes esters and salts such asammonium, isopropylammonium, potassium, sodium (including sesquisodium)and trimesium (alternatively named sulfosate).

“Photosystem I electron diverters” (b6) are chemical compounds thataccept electrons from Photosystem I, and after several cycles, generatehydroxyl radicals. These radicals are extremely reactive and readilydestroy unsaturated lipids, including membrane fatty acids andchlorophyll. This destroys cell membrane integrity, so that cells andorganelles “leak”, leading to rapid leaf wilting and desiccation, andeventually to plant death. Examples of this second type ofphotosynthesis inhibitor include diquat and paraquat.

“PPO inhibitors” (b7) are chemical compounds that inhibit the enzymeprotoporphyrinogen oxidase, quickly resulting in formation of highlyreactive compounds in plants that rupture cell membranes, causing cellfluids to leak out. Examples of PPO inhibitors includeacifluorfen-sodium, azafenidin, benzfendizone, bifenox, butafenacil,carfentrazone, carfentrazone-ethyl, chlomethoxyfen, cinidon-ethyl,fluazolate, flufenpyr-ethyl, flumiclorac-pentyl, flumioxazin,fluoroglycofen-ethyl, fluthiacet-methyl, fomesafen, halosafen, lactofen,oxadiargyl, oxadiazon, oxyfluorfen, pentoxazone, profluazol, pyraclonil,pyraflufen-ethyl, saflufenacil, sulfentrazone, thidiazimin,trifludimoxazin(dihydro-1,5-dimehyl-6-thioxo-3-[2,2,7-trifluoro-3,4-dihydro-3-oxo-4-(2-propyn-1-yl)-2H-1,4-benzoxazin-6-yl]-1,3,5-triazine-2,4(1H,3H)-dione)and tiafenacil (methylN-[2-[[2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl]thio]-1-oxopropyl]-β-alaninate).

“GS inhibitors” (b8) are chemical compounds that inhibit the activity ofthe glutamine synthetase enzyme, which plants use to convert ammoniainto glutamine. Consequently, ammonia accumulates and glutamine levelsdecrease. Plant damage probably occurs due to the combined effects ofammonia toxicity and deficiency of amino acids required for othermetabolic processes. The GS inhibitors include glufosinate and itsesters and salts such as glufosinate-ammonium and other phosphinothricinderivatives, glufosinate-P((2S)-2-amino-4-(hydroxymethylphosphinyl)butanoic acid) and bilanaphos.

“VLCFA elongase inhibitors” (b9) are herbicides having a wide variety ofchemical structures, which inhibit the elongase. Elongase is one of theenzymes located in or near chloroplasts which are involved inbiosynthesis of VLCFAs. In plants, very-long-chain fatty acids are themain constituents of hydrophobic polymers that prevent desiccation atthe leaf surface and provide stability to pollen grains. Such herbicidesinclude acetochlor, alachlor, anilofos, butachlor, cafenstrole,dimethachlor, dimethenamid, diphenamid, fenoxasulfone(3-[[(2,5-dichloro-4-ethoxyphenyl)methyl]sulfonyl]-4,5-dihydro-5,5-dimethylisoxazole),fentrazamide, flufenacet, indanofan, mefenacet, metazachlor,metolachlor, naproanilide, napropamide, napropamide-M((2R)—N,N-diethyl-2-(1-naphthalenyloxy)propanamide), pethoxamid,piperophos, pretilachlor, propachlor, propisochlor, pyroxasulfone, andthenylchlor, including resolved forms such as S-metolachlor andchloroacetamides and oxyacetamides.

“Auxin transport inhibitors” (b10) are chemical substances that inhibitauxin transport in plants, such as by binding with an auxin-carrierprotein. Examples of auxin transport inhibitors include diflufenzopyr,naptalam (also known as N-(1-naphthyl)phthalamic acid and2-[(1-naphthalenylamino)carbonyl]benzoic acid).

“PDS inhibitors” (b11) are chemical compounds that inhibit carotenoidbiosynthesis pathway at the phytoene desaturase step. Examples of PDSinhibitors include beflubutamid, diflufenican, fluridone,flurochloridone, flurtamone norflurzon and picolinafen.

“HPPD inhibitors” (b12) are chemical substances that inhibit thebiosynthesis of synthesis of 4-hydroxyphenyl-pyruvate dioxygenase.Examples of HPPD inhibitors include benzobicyclon, benzofenap,bicyclopyrone(4-hydroxy-3-[[2-[(2-methoxyethoxy)methyl]-6-(trifluoromethyl)-3-pyridinyl]carbonyl]bicyclo[3.2.1]oct-3-en-2-one),fenquinotrione(2-[[8-chloro-3,4-dihydro-4-(4-methoxyphenyl)-3-oxo-2-quinoxalinyl]carbonyl]-1,3-cyclohexanedione),isoxachlortole, isoxaflutole, mesotrione, pyrasulfotole, pyrazolynate,pyrazoxyfen, sulcotrione, tefuryltrione, tembotrione, tolpyralate(1-[[1-ethyl-4-[3-(2-methoxyethoxy)-2-methyl-4-(methylsulfonyl)benzoyl]-1H-pyrazol-5-yl]oxy]ethylmethyl carbonate), topramezone,5-chloro-3-[(2-hydroxy-6-oxo-1-cyclohexen-1-yl)carbonyl]-1-(4-methoxyphenyl)-2(1H)-quinoxalinone,4-(2,6-diethyl-4-methylphenyl)-5-hydroxy-2,6-dimethyl-3(2H)-pyridazinone,4-(4-fluorophenyl)-6-[(2-hydroxy-6-oxo-1-cyclohexen-1-yl)carbonyl]-2-methyl-1,2,4-triazine-3,5(2H,4H)-dione,5-[(2-hydroxy-6-oxo-1-cyclohexen-1-yl)carbonyl]-2-(3-methoxyphenyl)-3-(3-methoxypropyl)-4(3H)-pyrimidinone,2-methyl-N-(4-methyl-1,2,5-oxadiazol-3-yl)-3-(methylsulfinyl)-4-(trifluoromethyl)benzamideand2-methyl-3-(methylsulfonyl)-N-(1-methyl-1H-tetrazol-5-yl)-4-(trifluoromethyl)benzamide.

“HST inhibitors” (b13) disrupt a plant's ability to converthomogentisate to 2-methyl-6-solanyl-1,4-benzoquinone, thereby disruptingcarotenoid biosynthesis. Examples of HST inhibitors includecyclopyrimorate(6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl4-morpholinecarboxylate), haloxydine, pyriclor,3-(2-chloro-3,6-difluorophenyl)-4-hydroxy-1-methyl-1,5-naphthyridin-2(1H)-one,7-(3,5-dichloro-4-pyridinyl)-5-(2,2-difluoroethyl)-8-hydroxypyrido[2,3-b]pyrazin-6(5H)-oneand4-(2,6-diethyl-4-methylphenyl)-5-hydroxy-2,6-dimethyl-3(2H)-pyridazinone.

HST inhibitors also include compounds of Formulae A and B.

-   wherein R^(d1) is H, Cl or CF₃; R^(d2) is H, Cl or Br; R^(d3) is H    or Cl; R^(d4) is H, Cl or CF₃; R^(d5) is CH₃, CH₂CH₃ or CH₂CHF₂; and    R^(d6) is OH, or —OC(═O)-i-Pr; and R^(e1) is H, F, Cl, CH₃ or    CH₂CH₃; R^(e2) is H or CF₃; R^(e3) is H, CH₃ or CH₂CH₃; R^(e4) is H,    F or Br; R^(e5) is Cl, CH₃, CF₃, OCF₃ or CH₂CH₃; R^(e6) is H, CH₃,    CH₂CHF₂ or C≡CH; R^(e7) is OH, —OC(═O)Et, —OC(═O)-i-Pr or    —OC(═O)-t-Bu; and A^(e8) is N or CH.

“Cellulose biosynthesis inhibitors” (b14) inhibit the biosynthesis ofcellulose in certain plants. They are most effective when appliedpreemergence or early postemergence on young or rapidly growing plants.Examples of cellulose biosynthesis inhibitors include chlorthiamid,dichlobenil, flupoxam, indaziflam(N²-[(1R,2S)-2,3-dihydro-2,6-dimethyl-1H-inden-1-yl]-6-(1-fluoroethyl)-1,3,5-triazine-2,4-diamine),isoxaben and triaziflam.

“Other herbicides” (b15) include herbicides that act through a varietyof different modes of action such as mitotic disruptors (e.g.,flamprop-M-methyl and flamprop-M-isopropyl), organic arsenicals (e.g.,DSMA, and MSMA), 7,8-dihydropteroate synthase inhibitors, chloroplastisoprenoid synthesis inhibitors and cell-wall biosynthesis inhibitors.Other herbicides include those herbicides having unknown modes of actionor do not fall into a specific category listed in (b1) through (b14) oract through a combination of modes of action listed above. Examples ofother herbicides include aclonifen, asulam, amitrole, bromobutide,cinmethylin, clomazone, cumyluron, daimuron, difenzoquat, etobenzanid,fluometuron, flurenol, fosamine, fosamine-ammonium, dazomet, dymron,ipfencarbazone(1-(2,4-dichlorophenyl)-N-(2,4-difluorophenyl)-1,5-dihydro-N-(1-methylethyl)-5-oxo-4H-1,2,4-triazole-4-carboxamide),metam, methyldymron, oleic acid, oxaziclomefone, pelargonic acid,pyributicarb and5-[[(2,6-difluorophenyl)methoxy]methyl]-4,5-dihydro-5-methyl-3-(3-methyl-2-thienyl)isoxazole.

“Herbicide safeners” (b16) are substances added to a herbicideformulation to eliminate or reduce phytotoxic effects of the herbicideto certain crops. These compounds protect crops from injury byherbicides but typically do not prevent the herbicide from controllingundesired vegetation. Examples of herbicide safeners include but are notlimited to benoxacor, cloquintocet-mexyl, cumyluron, cyometrinil,cyprosulfamide, daimuron, dichlormid, dicyclonon, dietholate,dimepiperate, fenchlorazole-ethyl, fenclorim, flurazole, fluxofenim,furilazole, isoxadifen-ethyl, mefenpyr-diethyl, mephenate,methoxyphenone, naphthalic anhydride, oxabetrinil,N-(aminocarbonyl)-2-methylbenzenesulfonamide andN-(aminocarbonyl)-2-fluorobenzenesulfonamide,1-bromo-4-[(chloromethyl)sulfonyl]benzene,2-(dichloromethyl)-2-methyl-1,3-dioxolane (MG 191),4-(dichloroacetyl)-1-oxa-4-azospiro[4.5]decane (MON 4660),2,2-dichloro-1-(2,2,5-trimethyl-3-oxazolidinyl)-ethanone and2-methoxy-N-[[4-[[(methylamino)carbonyl]amino]phenyl]sulfonyl]-benzamide.

The compounds of Formula 1 can be prepared by general methods known inthe art of synthetic organic chemistry. One or more of the followingmethods and variations as described in Schemes 1-16 can be used toprepare the compounds of Formula 1. The definitions of (insertvariables) in the compounds of Formulae 1-25 below are as defined abovein the Summary of the Invention unless otherwise noted. Compounds ofFormulae 1A-1D are various subsets of the compounds of Formula 1, andall substituents for Formulae 1A-1D are as defined above for Formula 1unless otherwise noted. Compounds of Formulae 2A-2I are various subsetsof the compounds of Formula 1, and all substituents for Formulae 2A-2Iare as defined above for Formula 2 unless otherwise noted. Compounds ofFormulae 7A-7B are various subsets of the compounds of Formula 7, andall substituents for Formulae 7A-1B are as defined above for Formula 7unless otherwise noted.

As shown in Scheme 1 a compound of Formula 1 can be prepared bynucleophilic substitution by heating a compound of Formula 2 in asuitable solvent, such as acetonitrile, tetrahydrofuran orN,N-dimethylformamide in the presence of a base such as potassium orcesium carbonate, at temperatures ranging from 50 to 110° C., with acompound of Formula 3 (where LG is halogen or SO₂Me). The reaction istypically conducted at temperatures ranging from 50 to 110° C.

Alternatively, as shown in Scheme 2, boron compounds of Formula 5 or tincompounds of Formula 6 can be coupled with intermediates of Formula 4under Suzuki or Stille conditions to give compounds of carbon linkedcompounds of Formula 1. Suzuki couplings typically are conducted in thepresence of Pd(0) or Pd(II) salts, a suitable ligand, and a base.Suitable bases for this transformation include potassium carbonate orcesium carbonate, while Pd(II) salts such as Pd(OAc)₂ or PdCl₂ can beused in conjunction with ligands such as triphenylphosphine or1,1′-bis(diphenylphosphino)ferrocene (dppf). Conditions for Suzukicouplings are well documented in the literature (see for exampleAngewandte Chemie International Edition 2006, 45, 3484 and TetrahedronLetters 2002, 58(14), 2885). Boron intermediates of Formula 5 arecommercially available or can be prepared from the corresponding halidesor trifluoromethanesulfonates by methods known in the literature (seefor example PCT Patent Publication WO 2007/043278, U.S. Pat. No.8,080,566, Organic Letters 2011, 13(6), 1366 and Organic Letters 2012,14(2), 600). Stille couplings typically can be conducted in the presenceof Pd(0) or a Pd(II) salt, a ligand and a Cu(I) salt such as copper(I)iodide. The reaction can be run in a solvent such as dioxane,1,2-dimethoxyethane or toluene at a temperature ranging from ambient toreflux. For conditions and reagents employed in Stille couplings seeChemical Reviews 2007, 107(1), 133-173.

As shown in Scheme 3, a compound of Formula 2A (i.e. a compound ofFormula 2 wherein Z is O, R^(A) is H or lower alkyl and Q is aheterocycle connected via a nitrogen atom) can be prepared using aBuchwald copper(I) catalyzed carbon-nitrogen bond forming reaction inthe presence of a ligand such as ethylene diamine or cyclohexane diamineby heating a compound of Formula 7 (wherein X¹ is I or Br) in a suitablesolvent, such as toluene, 1,4-dioxanes or N,N-dimethylformamide in thepresence of a base such as potassium carbonate, cesium carbonate ortribasic potassium phosphate, with a compound of Formula 8 (i.e. anaromatic 5-membered heterocycle with a free NH group). The reaction istypically conducted at about 110° C. as described for copper-catalyzedcarbon-nitrogen bond formation methods using diamine ligands found inSurry and Buchwald, Chemical Science 2010, 1, 13-31. One skilled in theart can prepare a compound of Formula 8 by means found in ComrehensiveHeterocyclic Chemistry, Part II, 1996, parts 2, 3 & 4, Pergamon Press,publisher, edited by Alan. R. Katritzky & Charles W. Reese and CHC, PartI, 1984 and series of The Chemistry of Heterocyclic Compounds, 1981,publisher John Wiley & sons and Interscience Publishers Inc, 1953.

Phosphine ligands can also be employed for palladium-catalyzed aminationreactions to prepare a compound of Formula 2A. A review of suitableligands, bases, solvents, catalysts and substrates for use withNH-containing heterocycles (i.e. a compound of Formula 8) can be foundin Surry and Buchwald, Chemical Science 2011, 2, 27-50 and referencescited therein. In particular, conditions for pyrazoles and imidazoleswith aryl or heteroaryl halides using a palladium catalyst such asPd₂(dba)₃, with ligands such as2-di-t-butylphophino-2′,4′,6′-triisopropylbiphenyl (i.e. t-Bu-X-Phos) or2-di-t-butylphophino-3,4,5,6-tetramethyl-2′,4′,6′-triisopropylbiphenyl(i.e. Me₄-t-Bu-X-Phos) with bases such as Na⁺—O-t-Bu or K₃PO₄ insolvents such as toluene or 1,4-dioxane at temperatures ranging from 60to 105° C. are described. Alternative synthetic strategies can also befound in Sorokin, Mini-Reviews in Organic Chemistry 2008, 5, 323-330;Bellina and Rossi, Advanced Synthesis & Catalysis 2010, 352, 1223-1276,and Beletskaya and Cheprakov, Organometallics 2012, 31, 7753-7808.

As shown in Scheme 4, a compound of Formula 2B (i.e. a compound ofFormula 2 wherein Z is O, R^(A) is H or lower alkyl and Q is aheterocycle connected via a carbon atom) can also be prepared by directnucleophilic displacement by heating a compound of Formula 7A, (i.e. acompound of Formula 7 wherein X¹ is F or Cl) in a suitable solvent suchas N,N-dimethylformamide, N,N-dimethylacetamide or N-methylpyrrolidinoneand in the presence of a base such as potassium or cesium carbonate witha compound of Formula 5. The reaction is typically conducted attemperatures ranging from 80 to 160° C. but the transformation can beaccomplished at higher or lower temperatures depending on the nature ofthe R³ substituents and X¹.

As shown in Scheme 5, a compound of Formula 2D (i.e. a compound ofFormula 2 where Z is O and R^(A) is H) can be prepared by deprotectionof a compound of Formula 2C (i.e. a compound of Formula 2A wherein Z isO; and R^(A) is CH₃ or —C(═O)CH₃) with a suitable deprotecting agent.Suitable methoxy (i.e. when R^(A) is CH₃) deprotecting reagents such asBBr₃, AlCl₃ and HBr in acetic acid can be used in the presence ofsolvents such as toluene, dichloromethane and dichloroethane at atemperature of from −80 to 120° C. Suitable acetoxy (i.e. when R^(A) is—C(═O)CH₃) deprotecting agents include potassium carbonate in methanolor ammonium acetate in aqueous methanol at room temperature can be usedas discussed in Das, et al., Tetrahedron 2003, 59, 1049-1054 and methodscited therein. Alternatively, a compound of Formula 2C can be combinedwith Amberlyst 15© in methanol (as discussed in Das, et al. Tet. Lett.2003, 44, 5465-5468) or combined with sodium acetate in ethanol (asdiscussed in Narender, T., et al. Synthetic Communications 2009, 39(11),1949-1956) to obtain a compound of Formula 2D. Other useful phenolicprotecting groups suitable for use in preparing a compound of Formula 2Dcan be found in Greene, T. W.; Wuts, P. G. M. Protective Groups inOrganic Synthesis, 4th ed.; Wiley: Hoboken, N.J., 1991.

An intermediate of Formula 2C can be prepared as shown in Scheme 6 froman intermediate of Formula 9 by a variety of methods known to oneskilled in the art. Compounds of Formula 2C can be accessed by couplingprecursors of Formula 9 wherein J is Br, Cl, I ortrifluoromethanesulfonate with boronate or trialkyltin group-containingheterocycles (i.e compounds of Formula 5 or Formula 6 using the Suzukiconditions or the Stille conditions of Scheme 2).

Alternatively, compounds of Formula 9 wherein J is a boronate ortrialkyltin group may be coupled with halogen-substituted heterocyclesQ-X² wherein X² is Br or I, using the methods shown in Scheme 2 toafford compounds of Formula 2C. The skilled chemist will realize thatwith the prudent choice of groups X² and J in reactions involvingcompounds of Formula 9 and Q-X² can synthesize the intermediate 2Cutilizing various cross coupling procedures such as Kumada coupling,Hiyama coupling or Negishi coupling described in “Metal-CatalyzedCross-Coupling Reactions”, Eds. A. de Meijere and F. Diederich,Wiley-VCH, Weinheim, 2004, vols 1 and 2.

When J in Formula 9 is an alkene, alkyne, oxime, nitrile or ketone,various Q heterocycles can be prepared using methods described inKatritsky, Advances in Heterocyclic Chemistry, Vol. 1-104, Elsevier. Incases where regioisomeric mixtures are produced, the desired product canbe isolated using routing separation techniques known in the art.

As shown in Scheme 7, a compound of Formula 7B can be prepared bycoupling of phenols of Formula 10 with a compound of Formula 3 under thenucleophilic substitution conditions described in Scheme 1.

Chemistry based on “C—H activation” can also be used to prepare acompound of Formula 2E (i.e. a compound of Formula 2 wherein Z is O;R^(A) is —C(O)CH₃) as shown in Scheme 8 utilizing palladium(II) acetateand (diacetoxyiodo)benzene. Compounds of Formula 2E can be convertedinto compounds of Formula 2D by hydrolysis using aqueous acid or base. Acompound of Formula 2D can subsequently be converted via methodsdisclosed in Scheme 1 to provide a compound of Formula 1A (i.e. acompound of Formula 1 wherein Z is O). These methods are detailed inreviews of selective activation of C—H bonds in Chemical Reviews 2010,110, 575-1211 and references cited therein. Methods for “C—H activation”can also be found in Wencel-Delord et al., Nature Chemistry 2013, 5,369-375 and a series of reviews of “C—H activation” in Accounts ofChemical Research 2012, 45, 777-958 and references cited therein.

Similarly, chemistry based on “C—H activation” can be used to prepare acompound of Formulae 2F (i.e. a compound of Formula 2 wherein Z is S) asshown in Scheme 9. A compound of Formula 11 can first be converted to acompound of Formula 12 (wherein X⁴ is Br or I) by utilizing a stepwiseintroduction of substituents using “C—H activation”.

Iodides and bromides of Formula 12 can then be further functionalized bycopper mediated cross-coupling with thiourea as described in Qi,Junsheng, Chin. J. Chem. 2010, 28, 1441-1443 to provide the aryl thiolafter acidic deprotection. Palladium catalyzed cross-coupling reactionsof aryl halides can give protected thiols that can, in turn, bedeprotected under either acidic conditions or basic conditions (e.g.cesium fluoride) to provide a compound of Formula 2F. These conditionsare discussed in Organ, Michael G., Angew. Chem. Int. Ed. 2012, 51,3314-3322 and the references cited therein. Also, relevant conditionscan be found in Takashiro Itoh, J. Org. Chem. 2006, 71, 2203-2206. Acompound of Formula 2F can then be converted via methods disclosed inScheme 1 to provide a compound of Formula 1.

In Scheme 10, isoxazoles of Formulae 2G and 2H (i.e. a compound ofFormula 2 wherein Z is O, R^(A) is CH₃, Q is Q-18 and Q-20 and R^(1a)and R^(1b) are substituents on Q) can be synthesized beginning withcompounds of Formula 13 or 14. A compound of Formula 13 can be reactedwith ester 15 using a base such as sodium methoxide or sodium hydride ina solvent such as tetrahydrofuran to afford a compound of Formula 17.Conversely a compound of Formula 14 can be reacted with a compound ofFormula 16 under similar conditions to afford a compound of Formula 17.This type of reaction is commonly referred to as a ‘ClaisenCondensation’ and well known to those skilled in the art. Reaction of acompound of Formula 17 with hydroxylamine hydrochloride in solvents suchas ethanol, N,N-dimethylformamide, or tetrahdrofuran under neutral,acidic (example of acids: trifluoroacetic acid, hydrochloric acid,sulfuric acid) or basic (examples of bases: sodium hydroxide, sodiumacetate, pyridine) to give varying mixtures of 2G and 2H dependent uponthe nature of R^(1a) and R^(1b).

In Scheme 11, the phenol, 2D is reacted with N,N-dimethyl thiocarbamoylchloride in N,N-dimethylformamide in the presence of a strong tertiaryamine base such as 1,4-diazabicyclo[2.2.2]octane or N-methylmorpholinefor acidic phenols (for less-acidic phenols, prior deprotonation withsodium hydride may be advantageous) to form the O-arylN,N-dimethylthiocarbamate of Formula 18. Newman-Kwart rearrangement of acompound of Formula 18 at temperatures ranging from 200 to 300° C.provides the intermediate S-aryl dimethylthiocarbamate of Formula 19. Aone-pot deprotection of a compound of Formula 19 is readily achievedusing 10% aqueous sodium hydroxide or methanolic potassium hydroxide toafford the corresponding aryl thiol. Subsequent reaction with a compoundof Formula 3 at or slightly above room temperature provides the product1B (i.e. a compound of Formula 1 wherein Z is S). Methods forNewman-Kwart rearrangements are found in Lloyd-Jones, Guy C., Synthesis2008, 661-689.

Functionalization of the Q group of Compounds of Formula 1 orintermediates of Formula 2 may also be accomplished by means ofelectrophilic substitution. Reagents capable of electrophilicsubstitution such as N-halosuccinimides, sulfuryl halides and elementalhalogens can be used in compatible solvents such asN,N-dimethylformamide or acetonitrile at temperatures from 20 to 120° C.to introduce substituents at reactive positions of the Q group.

Functionalization of the Q group may also be accomplished by means ofsuitable cross-coupling methods as described in V. Snieckus et al.,Angew. Chem. Int. Ed. 2012, 51, 5062-5086 or Accounts of ChemicalResearch 2008, 41, 11, 1439-1564 and references cited therein. Thesemethods involve selection of an appropriate catalyst and reagent systemfor converting a R¹ halogen substituent. For palladium-catalyzed crosscoupling reactions suitable for use with these types of Q groups seeGribble and Li Eds., Palladium in Heterocyclic Chemistry Volume 1,Pergamon Press, 2000, Gribble and Li, Eds., Palladium in HeterocyclicChemistry Volume 2, Pergamon Press, 2007 and deMeijere and DiederichEds., Metal-Catalyzed Cross-Coupling Reactions, Second Edition, JohnWiley and Sons, 2004.

Products of Formula 2I (a compound of Formula 2 wherein Q is Q-47) canbe prepared by the methods shown in Scheme 12. Phenyl hydrazines ofFormula 20 can be reacted with glyoxal in acetic acid followed byhydroxyl amine in ethanol to form arylhydrazone oxime intermediates ofFormula 21. Reaction of a compound of Formula 21 in pyridine with acopper salt such as copper sulphate provides the 2-aryltriazole-1-oxideintermediates of Formula 22. Treatment of a compound of Formula 22 withtrimethyloxonium tetrafluoroborate yields a 1-methoxy-2-phenyltriazoliumsalts that can react with R¹ nucleophiles (for example halides, cyanidesor alkoxides) to produce a compound of Formula 2I, (i.e. a compound ofFormula 2 wherein Z is O and R^(A) is a suitable protecting group suchas benzyl or CH₃). This route can also be used for substituteddicarbonyl compounds or their monooximes in place of glyoxal whichresult in compounds of Formula 22 where R¹ can be various alkyls afterreduction of the N-oxide. For specific examples of this sequence with avariety of dicarbonyl compounds and nucleophiles, see M. Begtrup in J.Chem. Society, Perkin Trans. I 1981, 503-513 and Bull. Soc. Chim. Belg.1997, 106, 717-727.

As shown in Scheme 13 compounds of Formula 1C (a compound of Formula 1wherein Q is Q-46) can be prepared by the coupling of an alkyne with anazide of Formula 23. This type of reaction is commonly referred to as‘click chemistry’ and well known to those skilled in the art. A reviewof suitable conditions and catalysts for the coupling of alkynes withazides (i.e. a compound of Formula 23) can be found in Meldal and Tomoein Chemial Reviews 2008, 108, 2952-3015 and references cited therein.Suitable conditions generally include a copper catalyst with ligandssuch as halides and ascorbate in a variety of organic solvents such astert-butanol, methanol, dimethylsulfoxide, dimethyl formamide inaddition to water. The regioselectivitiy of this coupling can bedependent upon the nature of R¹ however this can be controlled with thechoice of reaction conditions such as metalating a terminal alkyne. Alsonote that the two R¹ groups on the alkyne need not be identical. For anexample see Krasinski, Fokin, and Sharpless in Organic Letters, 2004, 6,1237-1240.

As shown in Scheme 14, a compound of Formula 23 can be prepared from acompound of Formula 24 using the same methods as described in Scheme 1.

As shown in Scheme 15 compounds of Formula 24 can be prepared bydiazotisation of an amine of Formula 25 followed by substitution withazide using methods well known to those skilled in the art. Descriptionsof how this transformation can be achieve are described in Wu, Zhao,Lan, Cao, Liu, Jinag, and Li in The Journal of Organic Chemistry 2012,77, 4261-4270 or in Barral, Moorhouse, and Moses in Organic Letters2007, 9, 1809-1811. Examples of suitable reagents for diazotizationinclude sodium nitrite and tert-butyl nitrite, and suitable examples ofazide sources include sodium azide and trimethylsilyl azide.

As shown in Scheme 16 compounds of Formula 1 can be oxidized to providethe pyridine N-oxide compounds of Formula 1D) using methods well knownto those skilled in the art (see, for example, Smith, M. B.; March, J.March's Advanced Organic Chemistry, 6^(th) ed; John Wiley & Sons:Hoboken, N.J. and references therein). Examples of oxidants that can beused to achieve this transformation include peroxyacids, urea-H₂O₂ insolvents such as dichloromethane, methanol, tetrahydrofuran andacetonitrile. Alternatively oxidant-catalyst combinations can also beused to achieve for example, combination of ruthenium catalysts withoxidants such as O₂ or peroxides in solvents such as dichloromethane,methanol, tetrahydrofuran, acetonitrile, and water.

It is recognized by one skilled in the art that various functionalgroups can be converted into others to provide different compounds ofFormula 1. For a valuable resource that illustrates the interconversionof functional groups in a simple and straightforward fashion, seeLarock, R. C., Comprehensive Organic Transformations: A Guide toFunctional Group Preparations, 2nd Ed., Wiley-VCH, New York, 1999. Forexample, intermediates for the preparation of compounds of Formula 1 maycontain aromatic nitro groups, which can be reduced to amino groups, andthen be converted via reactions well known in the art such as theSandmeyer reaction, to various halides, providing compounds ofFormula 1. The above reactions can also in many cases be performed inalternate order

It is recognized that some reagents and reaction conditions describedabove for preparing compounds of Formula 1 may not be compatible withcertain functionalities present in the intermediates. In theseinstances, the incorporation of protection/deprotection sequences orfunctional group interconversions into the synthesis will aid inobtaining the desired products. The use and choice of the protectinggroups will be apparent to one skilled in chemical synthesis (see, forexample, Greene, T. W.; Wuts, P. G. M. Protective Groups in OrganicSynthesis, 2nd ed.; Wiley: New York, 1991). One skilled in the art willrecognize that, in some cases, after the introduction of a given reagentas depicted in any individual scheme, it may be necessary to performadditional routine synthetic steps not described in detail to completethe synthesis of compounds of Formula 1. One skilled in the art willalso recognize that it may be necessary to perform a combination of thesteps illustrated in the above schemes in an order other than thatimplied by the particular presented to prepare the compounds of Formula1.

One skilled in the art will also recognize that compounds of Formula 1and the intermediates described herein can be subjected to variouselectrophilic, nucleophilic, radical, organometallic, oxidation, andreduction reactions to add substituents or modify existing substituents.

Without further elaboration, it is believed that one skilled in the artusing the preceding description can utilize the present invention to itsfullest extent. The following non-limiting Examples are illustrative ofthe invention. Steps in the following Examples illustrate a procedurefor each step in an overall synthetic transformation, and the startingmaterial for each step may not have necessarily been prepared by aparticular preparative run whose procedure is described in otherExamples or Steps. Percentages are by weight except for chromatographicsolvent mixtures or where otherwise indicated. Parts and percentages forchromatographic solvent mixtures are by volume unless otherwiseindicated. ¹H NMR spectra are reported in ppm downfield fromtetramethylsilane; “s” means singlet, “d” means doublet, “t” meanstriplet, “q” means quartet, “m” means multiplet, “dd” means doublet ofdoublets, “dt” means doublet of triplets, and “br s” means broadsinglet. Mass spectra (MS) are reported as the molecular weight of thehighest isotopic abundance parent ion (M+1) formed by addition of H+(molecular weight of 1) to the molecule, or (M−1) formed by the loss ofH+ (molecular weight of 1) from the molecule, observed by using liquidchromatography coupled to a mass spectrometer (LCMS) using eitheratmospheric pressure chemical ionization (AP+) where “amu” stands forunified atomic mass units.

Example 1 Preparation of5-chloro-2-[[2-[5-(difluoromethyl)-3-isoxazolyl]-3-pyridinyl]oxy]pyrimidine(Compound 6) and5-chloro-2-[[2-[5-(difluoromethyl)-3-isoxazolyl]-1-oxido-3-pyridinyl]oxy]pyrimidine(Compound 8) Step A: Preparation of3-(3-fluoro-2-pyridinyl)-5-isoxazolemethanol

To a solution of 3-fluoropyridine-2-carbaldehyde (0.50 g, 4.0 mmol) inethanol (6 mL) was added hydroxylamine hydrochloride (0.42 g, 6.0 mmol)followed by sodium acetate (0.66 g, 8.0 mmol) and the reaction stirredfor 30 min at room temperature. The reaction was partitioned betweenethyl acetate and water, the organic phase was dried with magnesiumsulfate and concentrated under vacuum to provide the desired product(0.40 g) which was taken on directly in the next step. To a solution of3-fluoropyridine-2-carbaldehyde oxime (10.0 g, 71.4 mmol) in ethylacetate (100 mL) at 0° C. was added N-chlorosuccinamide (18.2 g, 214mmol). The mixture was stirred for 1 hr. Then propargylic alcohol (14.3g, 107.1 mmol) and sodium bicarbonate (6.12 g, 107.1 mmol) were addedand the reaction stirred at room temperature for 16 hours. The reactionmixture was partitioned with water, and the organic phase was washedwith water and saturated aqueous sodium chloride. The organic phase wasdried with magnesium sulfate and concentrated under vacuum. The residuewas purified by chromatography on silica gel, eluting with 20% ethylacetate in petroleum ether to afford the title compound (7.0 g).

¹H NMR (400 MHz, CDCl₃) δ 8.59-8.54 (m, 1H), 7.58 (t, 1H), 7.42 (dt,1H), 6.90 (s, 1H), 4.88 (d, 2H), 2.18 (br t, 1H). MS (M+H)=195

Step B: Preparation of3-(3-fluoro-2-pyridinyl)-5-isoxazolecarboxaldehyde

To a solution of 3-(3-fluoro-2-pyridinyl)-5-isoxazolemethanol (i.e. theproduct of Step A) (0.20 g, 1.0 mmol) in anhydrous dichloromethane (10mL) was added Dess Martin Periodinane(1,1,1-triacetoxy-1,1-dihydro-1,2-benziodoxol-3(1H)-one) (0.52 g, 1.2mmol) and the reaction stirred at room temperature for 2 hours. Thereaction was partitioned with water and washed with a saturated solutionof sodium bicarbonate. The organic phase was dried with magnesiumsulfate and concentrated under vacuum. The residue was purified bychromatography on silica gel, eluting with 20% ethyl acetate inpetroleum ether to afford the title compound (0.1 g).

¹H NMR (300 MHz, DMSO-d6) δ 10.01 (s, 1H), 8.66 (br d, 1H), 8.07-7.97(m, 1H), 7.86 (s, 1H), 7.71 (dt, 1H).

Step C: Preparation of3-(3-methoxy-2-pyridinyl)-5-isoxazolecarboxaldehyde

To a solution of 3-(3-fluoro-2-pyridinyl)-5-isoxazolecarboxaldehyde(i.e. the product of Step B) (0.50 g, 2.6 mmol) in methanol (10 mL) wasadded sodium methoxide in methanol solution (0.70 g, 13.0 mmol) and thereaction was heated to 90° C. for 7 hours. The reaction was partitionedbetween water and ethyl acetate, the organic phase was separated, driedwith magnesium sulfate, and concentrated under vacuum. The residue waspurified by chromatography on silica gel, eluting with 50% ethyl acetatein petroleum ether to afford the title compound (0.30 g).

¹H NMR (400 MHz, DMSO-d6) δ 9.98 (s, 1H), 8.34 (dd, 1H), 7.79-7.76 (m,1H) 7.76-7.71 (m, 1H), 7.61-7.55 (m, 1H), 3.94 (s, 3H). MS (M+H)=205

Step D: Preparation of2-[5-(difluoromethyl)-3-isoxazolyl]-3-methoxypyridine

To a solution of 3-(3-methoxy-2-pyridinyl)-5-isoxazolecarboxaldehyde(i.e. the product of Step C) (0.20 g, 0.97 mmol) in anhydrousdichloromethane (6.0 mL) was added diethylaminosulfur trifluoride (0.31g, 1.95 mmol) at 0° C. and the reaction was allowed to warm to roomtemperature over 45 minutes. The reaction was partitioned between waterand dichloromethane, the organic phase was collected, dried withmagnesium sulfate, and concentrated under vacuum. The residue waspurified by chromatography on silica gel, eluting with 50% ethyl acetatein petroleum ether to afford the title compound (40 mg).

¹H NMR (400 MHz, CDCl₃) δ 8.40-8.33 (m, 1H), 7.40 (d, 2H), 7.25-7.21 (m,1H), 6.99-6.65 (m, 1H), 3.99 (s, 3H). MS (M+H)=227

Step E: Preparation of 2-[5-(difluoromethyl)-3-isoxazolyl]-3-pyridinol

To a solution of 2-[5-(difluoromethyl)-3-isoxazolyl]-3-methoxypyridine(i.e. the product of Step D) (80 mg, 0.35 mmol) in anhydrousdichloromethane (6.0 mL) at 0° C. was added a 1 molar solution of borontribromide (0.44 g, 1.8 mmol) and the reaction was allowed to warm toroom temperature over 3 hours. The reaction was treated with ice,followed by partitioning between water and dichloromethane. The organicphase was collected, dried with magnesium sulfate, and concentratedunder vacuum. The residue was purified by chromatography on silica gel,eluting with 20% ethyl acetate in petroleum ether to afford the titlecompound (60 mg).

¹H NMR (400 MHz, CDCl₃) δ 9.02 (s, 1H), 8.30 (dd, 1H), 7.47-7.43 (m,1H), 7.38 (s, 1H), 7.33 (dd, 1H), 6.96-6.71 (s, 1H). MS (M+H)=213

Step F: Preparation of5-chloro-2-[[2-[5-(difluoromethyl)-3-isoxazolyl]-3-pyridinyl]oxy]pyrimidine

To a solution of 2-[5-(difluoromethyl)-3-isoxazolyl]-3-pyridinol (i.e.the product of Step E) (240 mg, 0.926 mmol) in dimethylformamide (5.0mL) was added 5-chloro-2-methylsulfonyl-pyrimidine (i.e.5-chloro-2-(methylsulfonyl)-pyrimidine) (260 mg, 1.39 mmol) and cesiumcarbonate (636 mg, 1.80 mmol) at 0° C., and the reaction was allowed towarm to room temperature over 45 minutes. The reaction was partitionedbetween water and ethyl acetate, the organic phase was collected andfurther washed with saturated aqueous sodium chloride. The organic phasewas dried with ma.gnesium sulfate, and concentrated under vacuum. Theresidue was purified by preparative high pressure liquid chromatography(silica gel column), eluting with 20% ethyl acetate in petroleum etherto afford the title compound, a compound of the present invention, as asolid (120 mg).

¹H NMR (400 MHz, CDCl₃) δ 8.72-8.65 (m, 1H), 8.45 (s, 2H), 7.70 (dd,1H), 7.53 (dd, 1H), 7.25 (br s, 1H), 6.92-6.58 (m, 1H). MS (M+H)=325

Step G: Preparation of5-chloro-2-[[2-[5-(difluoromethyl)-3-isoxazolyl]-1-oxido-3-pyridinyl]oxy]pyrimidine

To a solution of5-chloro-2-[[2-[5-(difluoromethyl)-3-isoxazolyl]-3-pyridinyl]oxy]-pyrimidine(i.e. the product of Step F) (20 mg, 0.060 mmol) in anhydrousdichloromethane (3 mL) was added m-chloroperoxybenzoic acid (11 mg,0.087 mmol) at 0° C., and the reaction was allowed to warm to roomtemperature for 48 hours. The reaction was partitioned between water andethyl acetate, the organic phase was collected and further washed with asaturated solution of sodium bicarbonate. The organic phase was driedwith magnesium sulfate, and concentrated under vacuum. The residue waswashed with pentane and diethyl ether to afford the title compound, acompound of the present invention, as a solid (10 mg).

¹H NMR (400 MHz, CDCl₃) δ 8.47 (s, 2H), 8.34-8.30 (m, 1H), 7.46-7.26 (m,3H), 6.89-6.61 (m, 1H). MS (M+H)=341

Example 2 Preparation of2-[[2-(4-bromo-1H-pyrazol-1-yl)-3-pyridinyl]oxy]-5-chloro-pyrimidine(Compound 1) Step A: Preparation of2-(4-bromo-1H-pyrazol-1-yl)-3-methoxypyridine

To a solution of 2-bromo-3-methoxy-pyridine (2.0 g, 10.63 mmol) and4-bromopyrazole (1.72 g, 11.70 mmol) in dimethylsulfoxide (20 mL) wasadded K₂CO₃ (4.42 g, 31.91 mmol), CuI (0.40 g, 2.12 mmol) and L-proline(0.62 g, 5.31 mmol). The mixture was stirred at 100° C. for 36 h under anitrogen atmosphere. The reaction mixture was cooled, diluted with water(200 mL) and extracted with ethyl acetate (3×200 mL). The combinedorganic phases were washed with water and saturated aqueous sodiumchloride, dried over Na₂SO₄, filtered and concentrated under reducedpressure. The resulting residue was purified by medium pressure liquidchromatography on silica gel eluted with 0 to 25% ethyl acetate inhexanes to yield the title compound (900 mg) as a pale brown solid.

¹H NMR (400 MHz, CDCl₃) δ 8.26 (s, 1H), 8.18 (d, 1H), 7.75 (s, 1H), 7.43(dd, 1H), 7.32-7.29 (m, 1H), 3.96 (s, 3H). mp=84-87° C.

Step B: Preparation of 2-(4-bromo-1H-pyrazol-1-yl)-3-pyridinol

To a solution of 2-(4-bromo-1H-pyrazol-1-yl)-3-methoxypyridine (i.e. theproduct of Step A) (0.9 g, 3.54 mmol) in dichloromethane (10 mL) wasadded borontribromide (1.77 g, 7.08 mmol) at 0° C. The reaction mixturewas stirred at ambient temperature for 15 h. The reaction mixture wasthen poured into ice-cold saturated NaHCO₃ solution and extracted withdichloromethane (3×50 mL). The combined organic phases were washed withsaturated aqueous sodium chloride and dried over anhydrous Na₂SO₄ andconcentrated under reduced pressure. The crude reaction product waswashed with pentane and diethyl ether to afford the title compound (0.45g) as an off white solid.

¹H NMR (400 MHz, CDCl₃) δ 11.08 (brs, 1H), 8.65 (s, 1H), 7.93 (dd, 1H),7.69 (s, 1H), 7.40 (dd, 1H), 7.17-7.14 (m, 1H). mp=91-93° C.

Step C: Preparation of2-[[2-(4-bromo-1H-pyrazol-1-yl)-3-pyridinyl]oxy]-5-chloro-pyrimidine

To a solution of 2-(4-bromo-1H-pyrazol-1-yl)pyridine-3-ol (i.e. theproduct of Step B) (0.35 g, 1.45 mmol) in N,N-dimethylformamide (5.0 mL)was added 2,5-dichloropyrimidine (0.22 g, 1.45 mmol) and potassiumcarbonate (0.60 g, 4.37 mmol). The reaction mixture was stirred at 70°C. for 3 h. The reaction mixture was cooled, poured in water (50 mL) andextracted with ethyl acetate (3×50 mL). The combined organic phases werewashed with water followed by saturated aqueous sodium chloride, driedover anhydrous Na₂SO₄ and concentrated under reduced pressure. Theresulting crude product was purified by medium pressure liquidchromatography on silica gel eluted with 0 to 35% ethyl acetate inhexanes to yield the title compound, a compound of the presentinvention, (140 mg) as an off white solid.

¹H NMR (400 MHz, CDCl₃) δ 8.50-8.40 (m, 4H), 7.72 (d, J=8.0, 1H), 7.40(brs, 2H). mp=129-131° C.

Example 3 Preparation of5-chloro-2-[(5-chloro[2,3′-bipyridin]-2′-yl)oxy]pyrimidine (Compound 12)Step A: Preparation of 5-chloro-2′-methoxy-2,3′-bipyridine

To a nitrogen degassed solution of3-methoxy-2-(tributylstannyl)-pyridine (0.34 g, 0.86 mmol) in toluene(5.0 mL) was added 2,5-dichloropyridine (0.14 g, 0.95 mmol), copperbromide (0.009 g, 0.06 mmol, 0.7 equiv), andtetrakis(triphenylphosphine)palladium (0.050 g, 0.043 mmol). Thesolution was heated to 100° C. under a nitrogen atmosphere for 18 h. Thereaction mixture was cooled to ambient tamerature and the solvent wasremoved under vacuum. The reustlting residue was purified by silica gelchromatography eluting with an ethyl acetate in hexanes (0 to 100%).Subsequent acid/base extraction removed further impurities to afford thetitle compound (0.056 g).

¹H NMR (500 MHz, CDCl₃) δ 8.71-8.76 (m, 1H), 8.36-8.40 (m, 1H),7.84-7.90 (m, 1H), 7.76 (m, 1H), 7.30-7.38 (m, 2H), 3.88-3.91 (m, 3H).

Step B: Preparation of 5′-chloro-[2,2′-bipyridin]-3-ol

To a solution of 5-chloro-2′-methoxy-2,3′-bipyridine (i.e. the productobtained in Step A, 0.056 g, 0.25 mmol) in dichloromethane (3 mL) wasadded 0.25 mL of a 1 M boron tribromide solution in dichloromethane. Thereaction mixture was stirred at ambient temperature for 18 h. Thereaction mixture was partitioned with saturated sodium bicarbonate andthe organic phase was dried with MgSO₄ and concentrated under vacuum.The resulting residue was dissolved in ethyl acetate and extracted into1 N sodium hydroxide. The aqueous phase was separated and neutralizedwith 1 N aqueous hydrochloric acid, and the precipitate was extractedinto ethyl acetate. The organic phase was dried with MgSO₄ andconcentrated under vacuum to afford the title compound (0.030 g).

¹H NMR (500 MHz, CDCl₃) δ 13.19-13.40 (bs, 1H), 8.58 (dd, 1H), 8.50 (dd,1H) 8.21 (dd, 1H), 7.89 (dd, 1H), 7.34 (dd, 1H), 7.23-7.28 (m, 1H).

Step C: Preparation of5-chloro-2-[(5-chloro[2,3′-bipyridin]-2′-yl)oxy]pyrimidine

To a solution of 5′-chloro-[2,2′-bipyridin]-3-ol (i.e. the product ofStep B, 0.030 g, 0.14 mmol) in N,N-dimethylformamide (2.0 mL) was added5-chloro-2-(methylsulfonyl)-pyrimidine (0.042 g, 0.22 mmol) andpotassium carbonate (0.021 g, 0.15 mmol) and the reaction stirred atambient temperature for 18 h. The solvent was removed from the reactionmixture under vacuum and the resulting residue purified by silica gelchromatography eluting with a methanol in dichloromethane (0 to 30%),followed by a ethyl acetate in hexanes (0 to 30%) to provide the titlecompound, a compound of the invention (0.0085 g).

¹H NMR (500 MHz, CDCl₃) δ 8.63-8.69 (m, 1H), 8.42 (s, 2H), 8.31-8.36 (m,1H) 8.03-8.11 (m, 1H), 7.69-7.74 (m, 1H), 7.65 (s, 1H), 7.44-7.49 (m,1H); MS [M+H]⁺=319

By the procedures described herein together with methods known in theart, the following compounds of Tables 1 to 778 can be prepared. Thefollowing abbreviations are used in the Tables which follow: t meanstertiary, s means secondary, n means normal, i means iso, c means cyclo,Me means methyl, Et means ethyl, Pr means propyl, Bu means butyl, i-Prmeans isopropyl, Bu means butyl, c-Pr cyclopropyl, c-Bu meanscyclobutyl, Ph means phenyl, OMe means methoxy, OEt means ethoxy, SMemeans methylthio, SEt means ethylthio, NHMe methylamino, —CN meanscyano, Py means pyridinyl, —NO₂ means nitro, tzl meand triazol, pzlmeans pyrazol, izl means imidazole, odzl means oxadiazol, tdzl meansthiadiazol and SO₂Me means methylsulfonyl.

TABLE 1

Q Q Q 3-CF₃-1H-pyrazol-1-yl 3-Me-1H-pyrazol-1-yl 3-F-1H-pyrazol-1-yl3-Br-1H-pyrazol-1-yl 4-CF₃-1H-pyrazol-1-yl 4-Me-1H-pyrazol-1-yl4-F-1H-pyrazol-1-yl 4-Br-1H-pyrazol-1-yl 5-CF₃-1H-pyrazol-1-yl5-Me-1H-pyrazol-1-yl 5-F-1H-pyrazol-1-yl 5-Br-1H-pyrazol-1-yl3-CHF₂-1H-pyrazol-1-yl 3-Et-1H-pyrazol-1-yl 3-Cl-1H-pyrazol-1-yl3-I-1H-pyrazol-1-yl 4-CHF₂-1H-pyrazol-1-yl 4-Et-1H-pyrazol-1-yl4-Cl-1H-pyrazol-1-yl 4-I-1H-pyrazol-1-yl 5-CHF₂-1H-pyrazol-1-yl5-Et-1H-pyrazol-1-yl 5-Cl-1H-pyrazol-1-yl 3-I-1H-pyrazol-1-yl3-OMe-1H-pyrazol-1-yl 3-CN-1H-pyrazol-1-yl 3-OCF₃-1H-pyrazol-1-yl3-OCHF₂-1H-pyrazol-1-yl 4-OMe-1H-pyrazol-1-yl 4-CN-1H-pyrazol-1-yl4-OCF₃-1H-pyrazol-1-yl 4-OCHF₂-1H-pyrazol-1-yl 5-OCF₃-1H-pyrazol-1-yl5-CN-1H-pyrazol-1-yl 5-OCF₃-1H-pyrazol-1-yl 5-OCHF₂-1H-pyrazol-1-yl3-C(═O)MeO-1H-pyrazol-1-yl 3-Ph-1H-pyrazol-1-yl3,5-di-Me-1H-pyrazol-1-yl 3,5-di-F-1H-pyrazol-1-yl4-C(═O)MeO-1H-pyrazol-1-yl 4-Ph-1H-pyrazol-1-yl3,5-di-CF₃-1H-pyrazol-1-yl 3,5-di-C1-1H-pyrazol-1-yl5-C(═O)MeO-1H-pyrazol-1-yl 5-Ph-1H-pyrazol-1-yl3,5-di-CHF₂-1H-pyrazol-1-yl 3,5-di-Br-1H-pyrazol-1-yl3-CF₃-5-Me-1H-pyrazol-1-yl 3,4-di-Me-1H-pyrazol-1-yl3,4-di-CF₃-1H-pyrazol-1-yl 3,4-di-Br-1H-pyrazol-1-yl3,4-di-C1-1H-pyrazol-1-yl 1H-pyrazol-1-yl 3-Me-1H-[1,2,4]triazol-1-yl3-CF₃-1H-[1,2,4]triazol-1-yl 3-CHF₂-1H-[1,2,4]triazol-1-yl3-F-1H-[1,2,4]triazol-1-yl 3-Cl-1H-[1,2,4]triazol-1-yl3-Br-1H-[1,2,4]triazol-1-yl 3,5-di-Cl-1H-[1,2,4]triazol-1-yl3,5-di-Br-1H-[1,2,4]triazol-1-yl 3-Ph-1H-[1,2,4]triazol-1-yl1H-[1,2,4]triazol-1-yl 4-Me-2H-[1,2,3]triazol-2-yl4-CF₃-2H-[1,2,3]triazol-2-yl 4-CHF₂-2H-[1,2,3]triazol-2-yl4-F-2H-[1,2,3]triazol-2-yl 4-Cl-2H-[1,2,3]triazol-2-yl4-Br-2H-[1,2,3]triazol-2-yl 4-Ph-2H-[1,2,3]triazol-2-yl4,5-di-Me-2H-[1,2,3]triazol-2-yl 4,5-di-CF₃-2H-[1,2,3]triazol-2-yl4,5-di-C1-2H-[1,2,3]triazol-2-yl 4,5-di-Br-2H-[1,2,3]triazol-2-yl2H-[1,2,3]triazol-2-yl 4-Me-1H-[1,2,3]triazol-1-yl4-CF₃-1H-[1,2,3]triazol-1-yl 4-CHF₂-1H-[1,2,3]triazol-1-yl4-F-1H-[1,2,3]triazol-1-yl 4-C1-1H-[1,2,3]triazol-1-yl4-Br-1H-[1,2,3]triazol-1-yl 4-Ph-1H-[1,2,3]triazol-1-yl1H-[1,2,3]triazol-1-yl 3-Me-1H-pyrrol-1-yl 3-CF₃-1H-pyrrol-1-yl3-CHF₂-1H-pyrrol-1-yl 3,4-di-Me-1H-pyrrol-1-yl 2,4-di-Me-1H-pyrrol-1-yl3,4-di-CF₃-1H-pyrrol-1-yl 2,4-di-CF₃-1H-pyrrol-1-yl3,4-di-Br-1H-pyrrol-1-yl 3,4-di-Cl-1H-pyrrol-1-yl 4-CHO-1H-pyrazol-1-yl4-CF₂CF₃-1H-pyrazol-1-yl 4-OCF₂CF₂H-1H-pyrazol-1-yl4-CH₂CF₃-1H-pyrazol-1-yl 4-OCH₂CF₃-1H-pyrazol-1-yl4-n-Pr-1H-pyrazol-1-yl 4-i-Pr-1H-pyrazol-1-yl 4-c-Pr-1H-pyrazol-1-yl4-Ethynyl-1H-pyrazol-1-yl 4-Vinyl-1H-pyrazol-1-yl4-Allyl-1H-pyrazol-1-yl 4-CH₂F-1H-pyrazol-1-yl 4-SFS-1H-pyrazol-1-yl4-OCH₂CCH-1H-pyrazol-1-yl 4-SCF₃-1H-pyrazol-1-yl 4-SCHF₂-1H-pyrazol-1-yl4-SOMe-1H-pyrazol-1-yl 4-SO₂Me-1H-pyrazol-1-yl 4-SO₂CF₃-1H-pyrazol-1-yl4-CH₂OCH₃-1H-pyrazol-1-yl 4-OCH₂CHCH₂-1H-pyrazol-1-yl4-CH₂SCH₃-1H-pyrazol-1-yl 4-CF₃-1H-imidazol-1-yl 4-F-1H-imidazol-1-yl4-Cl-1H-imidazol-1-yl 4-Br-1H-imidazol-1-yl 4-I-1H-imidazol-1-yl4-Me-1H-imidazol-1-yl 4-Et-1H-imidazol-1-yl 4-CHF₂-1H-imidazol-1-yl4-CHO-1H-imidazol-1-yl 4-CH₂CF₃-1H-imidazol-1-yl 4-OCF₃-1H-imidazol-1-ylIsoxazol-5-yl 4-Me-isoxazol-5-yl 5-CHO-isoxazol-3-yl 3-F-isoxazol-5-yl4-Et-isoxazol-5-yl 5-CN-isoxazol-3-yl 3-Cl-isoxazol-5-yl4-CF₃-isoxazol-5-yl 5-CH₂CN-isoxazol-3-yl 3-Br-isoxazol-5-yl4-CHF₂-isoxazol-5-yl 5-OMe-isoxazol-3-yl 3-I-isoxazol-5-yl4-CHO-isoxazol-5-yl 5-OCF₃-isoxazol-3-yl 3-Me-isoxazol-5-yl4-CN-isoxazol-5-yl 5-Ph-isoxazol-3-yl 3-Et-isoxazol-5-yl4-OMe-isoxazol-5-yl 4-F-isoxazol-3-yl 3-CF₃-isoxazol-5-yl4-OCF₃-isoxazol-5-yl 4-Cl-isoxazol-3-yl 3-CHF₂-isoxazol-5-yl4-Ph-isoxazol-5-yl 4-Br-isoxazol-3-yl 3-CHO-isoxazol-5-yl isoxazol-3-yl4-I-isoxazol-3-yl 3-CN-isoxazol-5-yl 5-F-isoxazol-3-yl4-Me-isoxazol-3-yl 3-OMe-isoxazol-5-yl 5-Cl-isoxazol-3-yl4-Et-isoxazol-3-yl 3-OCF₃-isoxazol-5-yl 5-Br-isoxazol-3-yl4-CF₃-isoxazol-3-yl 3-Ph-isoxazol-5-yl 5-I-isoxazol-3-yl4-CHF₂-isoxazol-3-yl 4-F-isoxazol-5-yl 5-Me-isoxazol-3-yl4-CHO-isoxazol-3-yl 4-Cl-isoxazol-5-3/1 5-Et-isoxazol-3-yl4-CN-isoxazol-3-yl 4-Br-isoxazol-5-yl 5-CF₃-isoxazol-3-yl4-OMe-isoxazol-3-yl 4-I-isoxazol-5-yl 5-CHF₂-isoxazol-3-yl4-OCF₃-isoxazol-3-yl 4-Ph-isoxazol-3-yl 5-CHF₂-isothiazol-3-yl5-Br-isoxazol-4-yl Isothiazol-5-yl 5-CHO-isothiazol-3-yl5-I-isoxazol-4-yl 3-F-isothiazol-5-yl 5-CN-isothiazol-3-yl5-Me-isoxazol-4-yl 3-Cl-isothiazol-5-yl 5-CH₂CN-isothiazol-3-yl5-Et-isoxazol-4-yl 3-Br-isothiazol-5-yl 5-OMe-isothiazol-3-yl5-CF₃-isoxazol-4-yl 3-I-isothiazol-5-yl 5-OCF₃-isothiazol-3-yl5-CHF₂-isoxazol-4-yl 3-Me-isothiazol-5-yl 5-Ph-isothiazol-3-yl5-CHO-isoxazol-4-yl 3-Et-isothiazol-5-yl 4-F-isothiazol-3-yl5-CN-isoxazol-4-yl 3-CF₃-isothiazol-5-yl 4-Cl-isothiazol-3-yl5-OMe-isoxazol-4-yl 3-CHF₂-isothiazol-5-yl 4-Br-isothiazol-3-yl5-OCF₃-isoxazol-4-yl 3-CHO-isothiazol-5-yl 4-I-isothiazol-3-yl5-Ph-isoxazol-4-yl 3-CN-isothiazol-5-yl 4-Me-isothiazol-3-ylIsothiazol-4-yl 3-OMe-isothiazol-5-yl 4-Et-isothiazol-3-yl3-F-isothiazol-4-yl 3-OCF₃-isothiazol-5-yl 4-CF₃-isothiazol-3-yl3-Cl-isothiazol-4-yl 3-Ph-isothiazol-5-yl 4-CHF₂-isothiazol-3-yl3-Br-isothiazol-4-yl 4-F-isothiazol-5-yl 4-CHO-isothiazol-3-yl3-I-isothiazol-4-yl 4-Cl-isothiazol-5-yl 4-CN-isothiazol-3-yl3-Me-isothiazol-4-yl 4-Br-isothiazol-5-yl 4-OMe-isothiazol-3-yl3-Et-isothiazol-4-yl 4-I-isothiazol-5-yl 4-OCF₃-isothiazol-3-yl3-CF₃-isothiazol-4-yl 4-Me-isothiazol-5-yl 4-Ph-isothiazol-3-yl3-CHF₂-isothiazol-4-yl 4-Et-isothiazol-5-yl Isoxazol-4-yl3-CHO-isothiazol-4-yl 4-CF₃-isothiazol-5-yl 3-F-isoxazol-4-yl3-CN-isothiazol-4-yl 4-CHF₂-isothiazol-5-yl 3-Cl-isoxazol-4-yl3-OMe-isothiazol-4-yl 4-CHO-isothiazol-5-yl 3-Br-isoxazol-4-yl3-OCF₃-isothiazol-4-yl 4-CN-isothiazol-5-yl 3-I-isoxazol-4-yl3-Ph-isothiazol-4-yl 4-OMe-isothiazol-5-yl 3-Me-isoxazol-4-yl5-F-isothiazol-4-yl 4-OCF₃-isothiazol-5-yl 3-Et-isoxazol-4-yl5-Cl-isothiazol-4-yl 4-Ph-isothiazol-5-yl 3-CF₃-isoxazol-4-yl5-Br-isothiazol-4-yl Isothiazol-3-yl 3-CHF₂-isoxazol-4-yl5-I-isothiazol-4-yl 5-F-isothiazol-3-yl 3-CHO-isoxazol-4-yl5-Me-isothiazol-4-yl 5-Cl-isothiazol-3-yl 3-CN-isoxazol-4-yl5-Et-isothiazol-4-yl 5-Br-isothiazol-3-yl 3-OMe-isoxazol-4-yl5-CF₃-isothiazol-4-yl 5-I-isothiazol-3-yl 3-OCF₃-isoxazol-4-yl5-CHF₂-isothiazol-4-yl 5-Me-isothiazol-3-yl 3-Ph-isoxazol-4-yl5-CHO-isothiazol-4-yl 5-Et-isothiazol-3-yl 5-F-isoxazol-4-yl5-CN-isothiazol-4-yl 5-CF₃-isothiazol-3-yl 5-Cl-isoxazol-4-yl5-OMe-isothiazol-4-yl 5-OCF₃-isothiazol-4-yl 5-Et-thiazol-2-yl4-Me-oxazol-5-yl 5-Ph-isothiazol-4-yl 5-CF₃-thiazol-2-yl4-CF₃-oxazol-5-yl oxazol-2-yl 5-CHF₂-thiazol-2-yl 4-CHF₂-oxazol-5-yl5-F-oxazol-2-yl 5-CHO-thiazol-2-yl 4-CN-oxazol-5-yl 5-Cl-oxazol-2-yl5-CN-thiazol-2-yl 4-OMe-oxazol-5-yl 5-Br-oxazol-2-yl5-CH₂CN-thiazol-2-yl 4-OCF₃-oxazol-5-yl 5-I-oxazol-2-yl5-OMe-thiazol-2-yl 4-Ph-oxazol-5-yl 5-Me-oxazol-2-yl 5-OCF₃-thiazol-2-ylThiazol-5-yl 5-Et-oxazol-2-yl 5-Ph-thiazol-2-yl 2-F-thiazol-5-yl5-CF₃-oxazol-2-yl 4-F-thiazol-2-yl 2-C1-thiazol-5-yl 5-CHF₂-oxazol-2-yl4-C1-thiazol-2-yl 2-Br-thiazol-5-yl 5-CHO-oxazol-2-yl 4-Br-thiazol-2-yl2-Me-thiazol-5-yl 5-CN-oxazol-2-yl 4-I-thiazol-2-yl 2-CF₃-thiazol-5-yl5-CH₂CN-oxazol-2-yl 4-Me-thiazol-2-yl 2-CHF₂-thiazol-5-yl5-OMe-oxazol-2-yl 4-Et-thiazol-2-yl 2-CN-thiazol-5-yl 5-OCF₃-oxazol-2-yl4-CF₃-thiazol-2-yl 2-OMe-thiazol-5-yl 5-Ph-oxazol-2-yl4-CHF₂-thiazol-2-yl 2-OCF₃-thiazol-5-yl 4-F-oxazol-2-yl4-CHO-thiazol-2-yl 2-Ph-thiazol-5-yl 4-Cl-oxazol-2-yl 4-CN-thiazol-2-yl4-F-thiazol-5-yl 4-Br-oxazol-2-yl 4-OMe-thiazol-2-yl 4-C1-thiazol-5-yl4-I-oxazol-2-yl 4-OCF₃-thiazol-2-yl 4-Br-thiazol-5-yl 4-Me-oxazol-2-yl4-Ph-thiazol-2-yl 4-Me-thiazol-5-yl 4-Et-oxazol-2-yl Oxazol-5-yl4-CF₃-thiazol-5-yl 4-CF₃-oxazol-2-yl 2-F-oxazol-5-yl 4-CHF₂-thiazol-5-yl4-CHF₂-oxazol-2-yl 2-Cl-oxazol-5-yl 4-CN-thiazol-5-yl 4-CHO-oxazol-2-yl2-Br-oxazol-5-yl 4-OMe-thiazol-5-yl 4-CN-oxazol-2-yl 2-Me-oxazol-5-yl4-OCF₃-thiazol-5-yl 4-OMe-oxazol-2-yl 2-CF₃-oxazol-5-yl4-Ph-thiazol-5-yl 4-OCF₃-oxazol-2-yl 2-CHF₂-oxazol-5-yl Oxazol-4-yl4-Ph-oxazol-2-yl 2-CN-oxazol-5-yl 2-F-oxazol-4-yl Thiazol-2-yl2-OMe-oxazol-5-yl 2-Cl-oxazol-4-yl 5-F-thiazol-2-yl 2-OCF₃-oxazol-5-yl2-Br-oxazol-4-yl 5-Cl-thiazol-2-yl 2-Ph-oxazol-5-yl 2-Me-oxazol-4-yl5-Br-thiazol-2-yl 4-F-oxazol-5-yl 2-CF₃-oxazol-4-yl 5-I-thiazol-2-yl4-Cl-oxazol-5-yl 2-CHF₂-oxazol-4-yl 5-Me-thiazol-2-yl 4-Br-oxazol-5-yl2-CN-oxazol-4-yl 2-OMe-oxazol-4-yl 4-F-1-Me-1H-izl-2-yl5-CF₃-1-Me-1H-izl-4-yl 2-OCF₃-oxazol-4-yl 4-Cl-1-Me-1H-izl-2-yl5-CHF₂-1-Me-1H-izl-4-yl 2-Ph-oxazol-4-yl 4-Br-1-Me-1H-izl-2-yl5-CN-1-Me-1H-izl-4-yl 5-F-oxazol-4-yl 1,4-di-Me-1H-izl-2-yl5-OMe-1-Me-1H-izl-4-yl 5-Cl-oxazol-4-yl 4-CF₃-1-Me-1H-izl-2-yl5-OCF₃-1-Me-1H-izl-4-yl 5-Br-oxazol-4-yl 4-CHF₂-1-Me-1H-izl-2-yl5-Ph-1-Me-1H-izl-4-yl 5-Me-oxazol-4-yl 4-CN-1-Me-1H-izl-2-yl 1H-izl-5-yl5-CF₃-oxazol-4-yl 4-OMe-1-Me-1H-izl-2-yl 1-Me-1H-izl-5-yl5-CHF₂-oxazol-4-yl 4-OCF₃-1-Me-1H-izl-2-yl 2-F-1-Me-1H-izl-5-yl5-CN-oxazol-4-yl 4-Ph-l-Me-1H-izl-2-yl 2-Cl-1-Me-1H-izl-5-yl5-OMe-oxazol-4-yl 5-F-1-Me-1H-izl-2-yl 2-Br-1-Me-1H-izl-5-yl5-OCF₃-oxazol-4-yl 5-Cl-1-Me-1H-izl-2-yl 1,2-di-Me-1H-izl-5-yl5-Ph-oxazol-4-yl 5-Br-1-Me-1H-izl-2-yl 2-CF₃-1-Me-1H-izl-5-ylThiazol-4-yl 1,5-di-Me-1H-izl-2-yl 2-CHF₂-1-Me-1H-izl-5-yl2-F-thiazol-4-yl 5-CF₃-1-Me-1H-izl-2-yl 2-CN-1-Me-1H-izl-5-yl2-Cl-thiazol-4-yl 5-CHF₂-1-Me-1H-izl-2-yl 2-OMe-1-Me-1H-izl-5-yl2-Br-thiazol-4-yl 5-CN-1-Me-1H-izl-2-yl 2-OCF₃-1-Me-1H-izl-5-yl2-Me-thiazol-4-yl 5-OMe-1-Me-1H-izl-2-yl 2-Ph-1-Me-1H-izl-5-yl2-CF₃-thiazol-4-yl 5-OCF₃-1-Me-1H-izl-2-yl 4-F-1-Me-1H-izl-5-yl2-CHF₂-thiazol-4-yl 5-Ph-1-Me-1H-izl-2-yl 4-Cl-1-Me-1H-izl-5-yl2-CN-thiazol-4-yl 1H-izl-4-yl 4-Br-1-Me-1H-izl-5-yl 2-OMe-thiazol-4-yl1-Me-1H-izl-4-yl 1,4-di-Me-1H-izl-5-yl 2-OCF₃-thiazol-4-yl2-F-1-Me-1H-izl-4-yl 4-CF₃-1-Me-1H-izl-5-yl 2-Ph-thiazol-4-yl2-Cl-1-Me-1H-izl-4-yl 4-CHF₂-1-Me-1H-izl-5-yl 5-F-thiazol-4-yl2-Br-1-Me-1H-izl-4-yl 4-CN-1-Me-1H-izl-5-yl 5-Cl-thiazol-4-yl1,2-di-Me-1H-izl-4-yl 4-OMe-1-Me-1H-izl-5-yl 5-Br-thiazol-4-yl2-CF₃-1-Me-1H-izl-4-yl 4-OCF₃-1-Me-1H-izl-5-yl 5-Me-thiazol-4-yl2-CHF₂-1-Me-1H-izl-4-yl 4-Ph-1-Me-1H-izl-5-yl 5-CF₃-thiazol-4-yl2-CN-1-Me-1H-izl-4-yl 1H-pzl-3-yl 5-CHF₂-thiazol-4-yl2-OMe-1-Me-1H-izl-4-yl 1-Me-1H-pzl-3-yl 5-CN-thiazol-4-yl2-OCF₃-1-Me-1H-izl-4-yl 4-F-1-Me-1H-pzl-3-yl 5-OMe-thiazol-4-yl2-Ph-1-Me-1H-izl-4-yl 4-Cl-1-Me-1H-pzl-3-yl 5-OCF₃-thiazol-4-yl5-F-1-Me-1H-izl-4-yl 4-Br-1-Me-1H-pzl-3-yl 5-Ph-thiazol-4-yl5-Cl-1-Me-1H-izl-4-yl 1,4-di-Me-1H-pzl-3-yl 1H-izl-2-yl5-Br-1-Me-1H-izl-4-yl 4-CF₃-1-Me-1H-pzl-3-yl 1-Me-1H-izl-2-yl1,5-di-Me-1H-izl-4-yl 4-CHF₂-1-Me-1H-pzl-3-yl 4-CN-1-Me-1H-pzl-3-yl1H-pzl-5-yl 2-CHF₂[1,3,4]odzl-5-yl 4-OMe-1-Me-1H-pzl-3-yl1-Me-1H-pzl-5-yl 2-CN-[1,3,4]odzl-5-yl 4-OCF₃-1-Me-1H-pzl-3-yl3-F-1-Me-1H-pzl-5-yl 2-OMe-[1,3,4]odzl-5-yl 4-Ph-1-Me-1H-pzl-3-yl3-Cl-1-Me-1H-pzl-5-yl 2-OCF₃[1,3,4]odzl-5-yl 5-F-1-Me-1H-pzl-3-yl3-Br-1-Me-1H-pzl-5-yl [1,3,4]tdzl-2-yl 5-Cl-1-Me-1H-pzl-3-yl1,3-di-Me-1H-pzl-5-yl 2-F-[1,3,4]tdzl-5-yl 5-Br-1-Me-1H-pzl-3-yl3-CF₃-1-Me-1H-pzl-5-yl 2-Cl-[1,3,4]tdzl-5-yl 1,5-di-Me-1H-pzl-3-yl3-CHF₂-1-Me-1H-pzl-5-yl 2-Br-[1,3,4]tdzl-5-yl 5-CF₃-1-Me-1H-pzl-3-yl3-CN-1-Me-1H-pzl-5-yl 2-Me-[1,3,4]tdzl-5-yl 5-CHF₂-1-Me-1H-pzl-3-yl3-OMe-1-Me-1H-pzl-5-yl 2-CF₃-[1,3,4]tdzl-5-yl 5-CN-1-Me-1H-pzl-3-yl3-OCF₃-1-Me-1H-pzl-5-yl 2-CHF₂-[1,3,4]tdzl-5-yl 5-OMe-1-Me-1H-pzl-3-yl3-Ph-1-Me-1H-pzl-5-yl 2-CN-[1,3,4]tdzl-5-yl 5-OCF₃-1-Me-1H-pzl-3-yl4-F-1-Me-1H-pzl-5-yl 2-OMe-[1,3,4]tdzl-5-yl 5-Ph-1-Me-1H-pzl-3-yl4-Cl-1-Me-1H-pzl-5-yl 2-OCF₃-[1,3,4]tdzl-5-yl 1H-pzl-4-yl4-Br-1-Me-1H-pzl-5-yl 4H-[1,2,4]tzl-3-yl 1-Me-1H-pzl-4-yl1,4-di-Me-1H-pzl-5-yl 4-Me-4H-[1,2,4]tzl-3-yl 3-F-1-Me-1H-pzl-4-yl4-CF₃-1-Me-1H-pzl-5-yl 3-F-4-Me-4H-[1,2,4]tzl-5-yl 3-Cl-1-Me-1H-pzl-4-yl4-CHF₂-1-Me-1H-pzl-5-yl 3-Cl-4-Me-4H-[1,2,4]tzl-5-yl3-Br-1-Me-1H-pzl-4-yl 4-CN-1-Me-1H-pzl-5-yl 3-Br-4-Me-4H-[1,2,4]tzl-5-yl1,3-di-Me-1H-pzl-4-yl 4-OMe-1-Me-1H-pzl-5-yl3,4-di-Me-4H-[1,2,4]tzl-5-yl 3-CF₃-1-Me-1H-pzl-4-yl4-OCF₃-1-Me-1H-pzl-5-yl 3-CF₃-4-Me-4H-[1,2,4]tzl-5-yl3-CHF₂-1-Me-1H-pzl-4-yl 4-Ph-1-Me-1H-pzl-5-yl3-CHF₂-4-Me-4-[1,2,4]tzl-5yl 3-CN-1-Me-1H-pzl-4-yl Thiophene-2-yl3-CN-4-Me-4H-[1,2,4]tzl-5-yl 3-OMe-1-Me-1H-pzl-4-yl Thiophene-3-yl3-OMe-4-Me-4H-[1,2,4]tzl-5-yl 3-OCF₃-1-Me-1H-pzl-4-yl Furan-2-yl3-OCF₃-4-Me-4H-[1,2,4]tzl-5yl 3-Ph-1-Me-1H-pzl-4-yl Furan-3-yl3-Ph-4-Me-4H-[1,2,4]tzl-5-yl 5-F-1-Me-1H-pzl-4-yl 1H-pyrrol-2-yl1H-[1,2,4]tzl-3-yl 5-Cl-1-Me-1H-pzl-4-yl 1-Me-1H-pyrrol-2-yl1-Me-1H-[1,2,4]tzl-3-yl 5-Br-1-Me-1H-pzl-4-yl 1H-pyrrol-3-yl5-F-1-Me-1H-[1,2,4]tzl-3-yl 1,5-di-Me-1H-pzl-4-yl 1-Me-1H-pyrrol-3-yl5-Cl-1-Me-1H-[1,2,4]tzl-3-yl 5-CF₃-1-Me-1H-pzl-4-yl [1,3,4]odzl-2-yl5-Br-1-Me-1H-[1,2,4]tzl-3-yl 5-CHF₂-1-Me-1H-pzl-4-yl 2-F[1,3,4]odzl-5-yl1,5-di-Me-1H-[1,2,4]tzl-3-yl 5-CN-1-Me-1H-pzl-4-yl 2-Cl1[,3,4]odzl-5-yl5-CF₃-1-Me-1H-[1,2,4]tzl-3-yl 5-OMe-1-Me-1H-pzl-4-yl2-Br[1,3,4]odzl-5-yl 5-CHF₂-1-Me-1H-[1,2,4]tzl-3yl5-OCF₃-1-Me-1H-pzl-4-yl 2-Me[1,3,4]odzl-5-yl5-CN-1-Me-1H-[1,2,4]tzl-3-yl 5-Ph-1-Me-1H-pzl-4-yl 2-CF₃[1,3,4]odzl-5-yl5-OMe-1-Me-1H-[1,2,4]tzl-3-yl 5-OCF₃-1-Me-1H-[1,2,4]tzl-3yl[1,2,4]tdzl-5-yl 5-Br[1,2,3]odzl-4-yl 5-Ph-1-Me-1H-[1,2,4]tzl-3-yl3-F-[1,2,4]tdzl-5-yl 5-Me-[1,2,3]odzl-4-yl 1H-[1,2,4]tzl-5-yl3-Cl-[1,2,4]tdzl-5-yl 5-CF₃-[1,2,3]odzl-4-yl 1-Me-1H-[1,2,4]tzl-5-yl3-Br-[1,2,4]tdzl-5-yl 5-CHF₂-[1,2,3]odzl-4-yl3-F-1-Me-1H-[1,2,4]tzl-5-yl 3-Me-[1,2,4]tdzl-5-yl 5-CN-[1,2,3]odzl-4-yl3-Cl-1-Me-1H-[1,2,4]tzl-5-yl 3-CF₃-[1,2,4]tdzl-5-yl5-OMe-[1,2,3]odzl-4-yl 3-Br-1-Me-1H-[1,2,4]tzl-5-yl3-CHF₂-[1,2,4]tdzl-5-yl 5-OCF₃-[1,2,3]odzl-4-yl1,3-di-Me-1H-[1,2,4]tzl-5-yl 3-CN-[1,2,4]tdzl-5-yl 5-Ph-[1,2,3]odzl-4-yl3-CF₃-1-Me-1H-[1,2,4]tzl-5-yl 3-OMe-[1,2,4]tdzl-5-yl [1,2,3]tdzl-5-yl3-CHF₂-1-Me-1H-[1,2,4]tzl-5yl 3-OCF₃-[1,2,4]tdzl-5-yl4-F-[1,2,3]tdzl-5-yl 3-CN-1-Me-1H-[1,2,4]tzl-5-yl 3-Ph-[1,2,4]tdzl-5-yl4-Cl-[1,2,3]tdzl-5-yl 3-OMe-1-Me-1H-[1,2,4]tzl-5-yl [1,2,4]tdzl-3-yl4-Br-[1,2,3]tdzl-5-yl 3-OCF₃-1-Me-1H-[1,2,4]tzl-5yl 5-F-[1,2,4]tdzl-3-yl4-Me-[1,2,3]tdzl-5-yl 3-Ph-1-Me-1H--[1,2,4]tzl-5-yl5-Cl-[1,2,4]tdzl-3-yl 4-CF₃-[1,2,3]tdzl-5-yl [1,2,4]odzl-5-yl5-Br-[1,2,4]tdzl-3-yl 4-CHF₂-[1,2,3]tdzl-5-yl 3-F-[1,2,4]odzl-5-yl5-Me-[1,2,4]tdzl-3-yl 4-CN-[1,2,3]tdzl-5-yl 3-Cl-[1,2,4]odzl-5-yl5-CF₃-[1,2,4]tdzl-3-yl 4-OMe-[1,2,3]tdzl-5-yl 3-Br-[1,2,4]odzl-5-yl5-CHF₂-[1,2,4]tdzl-3-yl 4-OCF₃-[1,2,3]tdzl-5-yl 3-Me-[1,2,4]odzl-5-yl5-CN-[1,2,4]tdzl-3-yl 4-Ph-[1,2,3]tdzl-5-yl 3-CF₃-[1,2,4]odzl-5-yl5-OMe-[1,2,4]tdzl-3-yl [1,2,3]tdzl-4-yl 3-CHF₂-[1,2,4]lodzl-5-yl5-OCF₃-[1,2,4]tdzl-3-yl 5-F-[1,2,3]tdzl-4-yl 3-CN-[1,2,4]odzl-5-yl5-Ph-[1,2,4]tdzl-3-yl 5-Cl-[1,2,3]tdzl-4-yl 3-OMe-[1,2,4]odzl-5-yl[1,2,3]odzl-5-yl 5-Br-[1,2,3]tdzl-4-yl 3-OCF₃-[1,2,4]lodzl-5-yl4-F-[1,2,3]odzl-5-yl 5-Me-[1,2,3]tdzl-4-yl 3-Ph-[1,2,4]odzl-5-yl4-Cl-[1,2,3]odzl-5-yl 5-CF₃[1,2,3]tdzl-4-yl [1,2,4]odzl-3-yl4-Br-[1,2,3]odzl-5-yl 5-CHF₂-[1,2,3]tdzl-4-yl 5-F-[1,2,4]odzl-3-yl4-Me-[1,2,3]odzl-5-yl 5-CN-[1,2,3]tdzl-4-yl 5-Cl-[1,2,4]odzl-3-yl4-CF₃-[1,2,3]odzl-5-yl 5-OMe-[1,2,3]tdzl-4-yl 5-Br-[1,2,4]odzl-3-yl4-CHF₂-[1,2,3]odzl-5-yl 5-OCF₃-[1,2,3]tdzl-4-yl 5-Me-[1,2,4]odzl-3-yl4-CN-[1,2,3]odzl-5-yl 5-Ph-[1,2,3]tdzl-4-yl 5-CF₃-[1,2,4]odzl-3-yl4-OMe-[1,2,3]odzl-5-yl 3H-[1,2,4]tzl-3-yl 5-CHF₂-[1,2,4]odzl-3-yl4-OCF₃-[1,2,3]odzl-5-yl 5-F-3H-[1,2,4]tzl-3-yl 5-CN-[1,2,4]odzl-3-yl4-Ph-[1,2,3]odzl-5-yl 5-C1-3H-[1,2,4]tzl-3-yl 5-OMe-[1,2,4]odzl-3-yl[1,2,3]odzl-4-yl 5-Br-3H-[1,2,4]tzl-3-yl 5-OCF₃-[1,2,4]odzl-3-yl5-F-[1,2,3]odzl-4-yl 5-Me-3H-[1,2,4]tzl-3-yl 5-Ph-[1,2,4]odzl-3-yl5-Cl-[1,2,3]odzl-4-yl 5-CF₃-3H-[1,2,4]tzl-3-yl 5-CHF₂-3H-[1,2,4]tzl-3-yl4-OCF₃-1H-[1,2,3]tzl-5-yl 3-I-pyridin-2-yl 5-CN-3H-[1,2,4]tzl-3-yl4-Ph-1H-[1,2,3]tzl-5-yl 3-Me-pyridin-2-yl 5-OMe-3H-[1,2,4]tzl-3-yl5-F-pyridin-2-yl 3-Et-pyridin-2-yl 5-OCF₃-3H-[1,2,4]tzl-3-yl5-Cl-pyridin-2-yl 3-CF₃-pyridin-2-yl 5-Ph-3H-[1,2,4]tzl-3-yl5-Br-pyridin-2-yl 3-CHF₂-pyridin-2-yl 1H-[1,2,3]tzl-4-yl5-I-pyridin-2-yl 3-CHO-pyridin-2-yl 5-F-1H-[1,2,3]tzl-4-yl5-Me-pyridin-2-yl 3-CN-pyridin-2-yl 5-Cl-1H-[1,2,3]tzl-4-yl5-Et-pyridin-2-yl 3-OMe-pyridin-2-yl 5-Br-1H-[1,2,3]tzl-4-yl5-CF₃-pyridin-2-yl 3-OCF₃-pyridin-2-yl 5-Me-1H-[1,2,3]tzl-4-yl5-CHF₂-pyridin-2-yl 3-N(Me)₂-pyridin-2-yl 5-CF₃-1H-[1,2,3]tzl-4-yl5-CHO-pyridin-2-yl 3-Ph-pyridin-2-yl 5-CHF₂-1H-[1,2,3]tzl-4-yl5-CN-pyridin-2-yl 5,6-di-Cl-pyridin-2-yl 5-CN-1H-[1,2,3]tzl-4-yl5-OMe-pyridin-2-yl 6-F-pyridin-3-yl 5-OMe-1H-[1,2,3]tzl-4-yl5-OCF₃-pyridin-2-yl 6-Cl-pyridin-3-yl 5-OCF₃-1H-[1,2,3]tzl-4-yl5-N(Me)₂-pyridin-2-yl 6-Br-pyridin-3-yl 5-Ph-1H-[1,2,3]tzl-4-yl5-Ph-pyridin-2-yl 6-I-pyridin-3-yl 2H-[1,2,3]tzl-4-yl3,5-di-Cl-pyridin-2-yl 6-Me-pyridin-3-yl 4-F-2H-[1,2,3]tzl-5-yl3-Me-5-Cl-pyridin-2-yl 6-Et-pyridin-3-yl 4-Cl-2H-[1,2,3]tzl-5-yl3-CN-5-Cl-pyridin-2-yl 6-CF₃-pyridin-3-yl 4-Br-2H-[1,2,3]tzl-5-yl6-F-pyridin-2-yl 6-CHF₂-pyridin-3-yl 4-Me-2H-[1,2,3]tzl-5-yl6-Cl-pyridin-2-yl 6-CHO-pyridin-3-yl 4-CF₃-2H-[1,2,3]tzl-5-yl6-Br-pyridin-2-yl 6-CN-pyridin-3-yl 4-CHF₂-2H-[1,2,3]tzl-5-yl6-I-pyridin-2-yl 6-OMe-pyridin-3-yl 4-CN-2H-[1,2,3]tzl-5-yl6-Me-pyridin-2-yl 6-OCF₃-pyridin-3-yl 4-OMe-2H-[1,2,3]tzl-5-yl6-Et-pyridin-2-yl 6-N(Me)₂-pyridin-3-yl 4-OCF₃-2H-[1,2,3]tzl-5-yl6-CF₃-pyridin-2-yl 6-Ph-pyridin-3-yl 4-Ph-2H-[1,2,3]tzl-5-yl6-CHF₂-pyridin-2-yl 4,6-di-Cl-pyridin-3-yl 1H-[1,2,3]tzl-5-yl6-CHO-pyridin-2-yl 4-CN-6-Cl-pyridin-3-yl 4-F-1H-[1,2,3]tzl-5-yl6-CN-pyridin-2-yl 3-F-pyridin-4-yl 4-Cl-1H-[1,2,3]tzl-5-yl6-OMe-pyridin-2-yl 3-Cl-pyridin-4-yl 4-Br-1H-[1,2,3]tzl-5-yl6-OCF₃-pyridin-2-yl 3-Br-pyridin-4-yl 4-Me-1H--[1,2,3]tzl-5-yl6-N(Me)₂-pyridin-2-yl 3-I-pyridin-4-yl 4-CF₃-1H-[1,2,3]tzl-5-yl6-Ph-pyridin-2-yl 3-Me-pyridin-4-yl 4-CHF₂-1H-[1,2,3]tzl-5-yl3-F-pyridin-2-yl 3-Et-pyridin-4-yl 4-CN-1H-[1,2,3]tzl-5-yl3-Cl-pyridin-2-yl 3-CF₃-pyridin-4-yl 4-OMe-1H-[1,2,3]tzl-5-yl3-Br-pyridin-2-yl 3-CHF₂-pyridin-4-yl 3-CHO-pyridin-4-yl6-OCF₃-pyridazin-4-yl 2-Br-pyrimidin-5-yl 3-CN-pyridin-4-yl6-N(Me)₂-pyridazin-4-yl 2-I-pyrimidin-5-yl 3-OMe-pyridin-4-yl6-Ph-pyridazin-4-yl 2-Me-pyrimidin-5-yl 3-OCF₃-pyridin-4-yl4-Cl-pyridazin-4-yl 2-Et-pyrimidin-5-yl 3-N(Me)₂-pyridin-4-yl4-CN-pyridazin-4-yl 2-CF₃-pyrimidin-5-yl 3-Ph-pyridin-4-yl5-F-pyridazin-2-yl 2-CHF₂-pyrimidin-5-yl 3,5-di-Me-pyridin-4-yl5-Cl-pyridazin-2-yl 2-CHO-pyrimidin-5-yl 3,5-di-Cl-pyridin-4-yl5-Br-pyridazin-2-yl 2-CN-pyrimidin-5-yl 6-F-pyridazin-3-yl5-I-pyridazin-2-yl 2-OMe-pyrimidin-5-yl 6-Cl-pyridazin-3-yl5-Me-pyridazin-2-yl 2-OCF₃-pyrimidin-5-yl 6-Br-pyridazin-3-yl5-Et-pyridazin-2-yl 2-N(Me)₂-pyrimidin-5-yl 6-I-pyridazin-3-yl5-CF₃-pyridazin-2-yl 2-Ph-pyrimidin-5-yl 6-Me-pyridazin-3-yl5-CHF₂-pyridazin-2-yl 3-Cl-pyrazin-2-yl 6-Et-pyridazin-3-yl5-CHO-pyridazin-2-yl 3-CN-pyrazin-2-yl 6-CF₃-pyridazin-3-yl5-CN-pyridazin-2-yl 3-OMe-pyrazin-2-yl 6-CHF₂-pyridazin-3-yl5-OMe-pyridazin-2-yl 3-C1-[1,2,4]triazin-6-yl 6-CHO-pyridazin-3-yl5-OCF₃-pyridazin-2-yl 3-CN-[1,2,4]triazin-6-yl 6-CN-pyridazin-3-yl5-N(Me)₂-pyridazin-2-yl 3-OMe-[1,2,4]triazin-6-yl 6-OMe-pyridazin-3-yl5-Ph-pyridazin-2-yl 3-CF₃-[1,2,4]triazin-6-yl 6-OCF₃-pyridazin-3-yl5-F-pyrimidin-4-yl 6-Cl-[1,2,4]triazin-5-yl 6-N(Me)₂-pyridazin-3-yl5-Cl-pyrimidin-4-yl 6-Me-[1,2,4]triazin-5-yl 6-Ph-pyridazin-3-yl5-Br-pyrimidin-4-yl 6-OMe-[1,2,4]triazin-5-yl 4-Cl-pyridazin-3-yl5-I-pyrimidin-4-yl 6-CN-[1,2,4]triazin-5-yl 4-CN-pyridazin-3-yl5-Me-pyrimidin-4-yl 6-Cl-[1,2,4]triazin-3-yl 6-F-pyridazin-4-yl5-Et-pyrimidin-4-yl 6-Me-[1,2,4]triazin-3-yl 6-Cl-pyridazin-4-yl5-CF₃-pyrimidin-4-yl 6-OMe-[1,2,4]triazin-3-yl 6-Br-pyridazin-4-yl5-CHF₂-pyrimidin-4-yl 6-CN-[1,2,4]triazin-3-yl 6-I-pyridazin-4-yl5-CHO-pyrimidin-4-yl 4-Cl-[1,3,5]triazin-2-yl 6-Me-pyridazin-4-yl5-CN-pyrimidin-4-yl 2-Me-pyrimidin-5-yl 6-Et-pyridazin-4-yl5-OMe-pyrimidin-4-yl 4-OMe-1H-imidazol-1-yl 6-CF₃-pyridazin-4-yl5-OCf₃-pyrimidin-4-yl 6-CHF₂-pyridazin-4-yl 5-N(Me)₂-pyrimidin-4-yl6-CHO-pyridazin-4-yl 5-Ph-pyrimidin-4-yl 6-CN-pyridazin-4-yl2-F-pyrimidin-5-yl 6-OMe-pyridazin-4-yl 2-Cl-pyrimidin-5-yl

The present disclosure also includes Tables 2 through 778. Each Table isconstructed in the same manner as Table 1 above, except that the rowheading in Table 1 (i.e. “R²═Cl; Z═O; and R³═H (m=0).”) is replaced withthe respective row heading shown below.

Table Header Row 2 R² = F, Z = O, R³ = H (m = 0) 3 R² = F, Z = O, R³ =4-F 4 R² = F, Z = O, R³ = 4-Cl 5 R² = F, Z = O, R³ = 4-Br 6 R² = F, Z =O, R³ = 4-I 7 R² = F, Z = O, R³ = 4-CN 8 R² = F, Z = O, R³ = 4-NO₂ 9 R²= F, Z = O, R³ = 4-OMe 10 R² = F, Z = O, R³ = 4-OCF₃ 11 R² = F, Z = O,R³ = 4-CF₃ 12 R² = F, Z = O, R³ = 4-CHF₂ 13 R² = F, Z = O, R³ = 4-CH₂F14 R² = F, Z = O, R³ = 4-CHO 15 R² = F, Z = O, R³ = 4-Me 16 R² = F, Z =O, R³ = 4-Et 17 R² = F, Z = O, R³ = 4-Ethynyl 18 R² = F, Z = O, R³ =4-Ethenyl 19 R² = F, Z = O, R³ = 4-SO₂Me 20 R² = F, Z = O, R³ = 4-OAc 21R² = F, Z = O, R³ = 4-c-Pr 22 R² = F, Z = O, R³ = 4-i-Pr 23 R² = F, Z =O, R³ = 4-Ph 24 R² = F, Z = O, R³ = 5-F 25 R² = F, Z = O, R³ = 5-Cl 26R² = F, Z = O, R³ = 5-Br 27 R² = F, Z = O, R³ = 5-I 28 R² = F, Z = O, R³= 5-CN 29 R² = F, Z = O, R³ = 5-NO₂ 30 R² = F, Z = O, R³ = 5-OMe 31 R² =F, Z = O, R³ = 5-OCF₃ 32 R² = F, Z = O, R³ = 5-CF₃ 33 R² = F, Z = O, R³= 5-CHF₂ 34 R² = F, Z = O, R³ = 5-CH₂F 35 R² = F, Z = O, R³ = 5-CHO 36R² = F, Z = O, R³ = 5-Me 37 R² = F, Z = O, R³ = 5-Et 38 R² = F, Z = O,R³ = 5-Ethynyl 39 R² = F, Z = O, R³ = 5-Ethenyl 40 R² = F, Z = O, R³ =5-SO₂Me 41 R² = F, Z = O, R³ = 5-OAc 42 R² = F, Z = O, R³ = 5-c-Pr 43 R²= F, Z = O, R³ = 5-i-Pr 44 R² = F, Z = O, R³ = 5-Ph 45 R² = F, Z = O, R³= 6-F 46 R² = F, Z = O, R³ = 6-Cl 47 R² = F, Z = O, R³ = 6-Br 48 R² = F,Z = O, R³ = 6-I 49 R² = F, Z = O, R³ = 6-CN 50 R² = F, Z = O, R³ = 6-NO₂51 R² = F, Z = O, R³ = 6-OMe 52 R² = F, Z = O, R³ = 6-OCF₃ 53 R² = F, Z= O, R³ = 6-CF₃ 54 R² = F, Z = O, R³ = 6-CHF₂ 55 R² = F, Z = O, R³ =6-CH₂F 56 R² = F, Z = O, R³ = 6-CHO 57 R² = F, Z = O, R³ = 6-Me 58 R² =F, Z = O, R³ = 6-Et 59 R² = F, Z = O, R³ = 6-Ethynyl 60 R² = F, Z = O,R³ = 6-Ethenyl 61 R² = F, Z = O, R³ = 6-SO₂Me 62 R² = F, Z = O, R³ =6-OAc 63 R² = F, Z = O, R³ = 6-c-Pr 64 R² = F, Z = O, R³ = 6-i-Pr 65 R²= F, Z = O, R³ = 6-Ph 66 R² = F, Z = O, R³ = 4,5-di-F 67 R² = F, Z = O,R³ = 4,5-di-Cl 68 R² = F, Z = O, R³ = 4,5-di-Br 69 R² = F, Z = O, R³ =4,5-di-CN 70 R² = F, Z = O, R³ = 4,5-di-Me 71 R² = F, Z = O, R³ =4,5-di-OMe 72 R² = F, Z = O, R³ = 4,5-di-CF₃ 73 R² = Br, Z = O, R³ = 4-F74 R² = Br, Z = O, R³ = 4-Cl 75 R² = Br, Z = O, R³ = 4-Br 76 R² = Br, Z= O, R³ = 4-I 77 R² = Br, Z = O, R³ = 4-CN 78 R² = Br, Z = O, R³ = 4-NO₂79 R² = Br, Z = O, R³ = 4-OMe 80 R² = Br, Z = O, R³ = 4-OCF₃ 81 R² = Br,Z = O, R³ = 4-CF₃ 82 R² = Br, Z = O, R³ = 4-CHF₂ 83 R² = Br, Z = O, R³ =4-CH₂F 84 R² = Br, Z = O, R³ = 4-CHO 85 R² = Br, Z = O, R³ = 4-Me 86 R²= Br, Z = O, R³ = 4-Et 87 R² = Br, Z = O, R³ = 4-Ethynyl 88 R² = Br, Z =O, R³ = 4-Ethenyl 89 R² = Br, Z = O, R³ = 4-SO₂Me 90 R² = Br, Z = O, R³= 4-OAc 91 R² = Br, Z = O, R³ = 4-c-Pr 92 R² = Br, Z = O, R³ = 4-i-Pr 93R² = Br, Z = O, R³ = 4-Ph 94 R² = Br, Z = O, R³ = 5-F 95 R² = Br, Z = O,R³ = 5-Cl 96 R² = Br, Z = O, R³ = 5-Br 97 R² = Br, Z = O, R³ = 5-I 98 R²= Br, Z = O, R³ = 5-CN 99 R² = Br, Z = O, R³ = 5-NO₂ 100 R² = Br, Z = O,R³ = 5-OMe 101 R² = Br, Z = O, R³ = 5-OCF₃ 102 R² = Br, Z = O, R³ =5-CF₃ 103 R² = Br, Z = O, R³ = 5-CHF₂ 104 R² = Br, Z = O, R³ = 5-CH₂F105 R² = Br, Z = O, R³ = 5-CHO 106 R² = Br, Z = O, R³ = 5-Me 107 R² =Br, Z = O, R³ = 5-Et 108 R² = Br, Z = O, R³ = 5-Ethynyl 109 R² = Br, Z =O, R³ = 5-Ethenyl 110 R² = Br, Z = O, R³ = 5-SO₂Me 111 R² = Br, Z = O,R³ = 5-OAc 112 R² = Br, Z = O, R³ = 5-c-Pr 113 R² = Br, Z = O, R³ =5-i-Pr 114 R² = Br, Z = O, R³ = 5-Ph 115 R² = Br, Z = O, R³ = 6-F 116 R²= Br, Z = O, R³ = 6-Cl 117 R² = Br, Z = O, R³ = 6-Br 118 R² = Br, Z = O,R³ = 6-I 119 R² = Br, Z = O, R³ = 6-CN 120 R² = Br, Z = O, R³ = 6-NO₂121 R² = Br, Z = O, R³ = 6-OMe 122 R² = Br, Z = O, R³ = 6-OCF₃ 123 R² =Br, Z = O, R³ = 6-CF₃ 124 R² = Br, Z = O, R³ = 6-CHF₂ 125 R² = Br, Z =O, R³ = 6-CH₂F 126 R² = Br, Z = O, R³ = 6-CHO 127 R² = Br, Z = O, R³ =6-Me 128 R² = Br, Z = O, R³ = 6-Et 129 R² = Br, Z = O, R³ = 6-Ethynyl130 R² = Br, Z = O, R³ = 6-Ethenyl 131 R² = Br, Z = O, R³ = 6-SO₂Me 132R² = Br, Z = O, R³ = 6-OAc 133 R² = Br, Z = O, R³ = 6-c-Pr 134 R² = Br,Z = O, R³ = 6-i-Pr 135 R² = Br, Z = O, R³ = 6-Ph 136 R² = Br, Z = O, R³= 4,5-di-F 137 R² = Br, Z = O, R³ = 4,5-di-Cl 138 R² = Br, Z = O, R³ =4,5-di-Br 139 R² = Br, Z = O, R³ = 4,5-di-CN 140 R² = Br, Z = O, R³ =4,5-di-OMe 141 R² = Br, Z = O, R³ = 4,5-di-CF₃ 142 R² = Cl, Z = O, R³ =H (m = 0) 143 R² = Cl, Z = O, R³ = 4-F 144 R² = Cl, Z = O, R³ = 4-Cl 145R² = Cl, Z = O, R³ = 4-Br 146 R² = Cl, Z = O, R³ = 4-I 147 R² = Cl, Z =O, R³ = 4-CN 148 R² = Cl, Z = O, R³ = 4-NO₂ 149 R² = Cl, Z = O, R³ =4-OMe 150 R² = Cl, Z = O, R³ = 4-OCF₃ 151 R² = Cl, Z = O, R³ = 4-CF₃ 152R² = Cl, Z = O, R³ = 4-CHF₂ 153 R² = Cl, Z = O, R³ = 4-CH₂F 154 R² = Cl,Z = O, R³ = 4-CHO 155 R² = Cl, Z = O, R³ = 4-Me 156 R² = Cl, Z = O, R³ =4-Et 157 R² = Cl, Z = O, R³ = 4-Ethynyl 158 R² = Cl, Z = O, R³ =4-Ethenyl 159 R² = Cl, Z = O, R³ = 4-SO₂Me 160 R² = Cl, Z = O, R³ =4-OAc 161 R² = Cl, Z = O, R³ = 4-c-Pr 162 R² = Cl, Z = O, R³ = 4-i-Pr163 R² = Cl, Z = O, R³ = 4-Ph 164 R² = Cl, Z = O, R³ = 5-F 165 R² = Cl,Z = O, R³ = 5-Cl 166 R² = Cl, Z = O, R³ = 5-Br 167 R² = Cl, Z = O, R³ =5-I 168 R² = Cl, Z = O, R³ = 5-CN 169 R² = Cl, Z = O, R³ = 5-NO₂ 170 R²= Cl, Z = O, R³ = 5-OMe 171 R² = Cl, Z = O, R³ = 5-OCF₃ 172 R² = Cl, Z =O, R³ = 5-CF₃ 173 R² = Cl, Z = O, R³ = 5-CHF₂ 174 R² = Cl, Z = O, R³ =5-CH₂F 175 R² = Cl, Z = O, R³ = 5-CHO 176 R² = Cl, Z = O, R³ = 5-Me 177R² = Cl, Z = O, R³ = 5-Et 178 R² = Cl, Z = O, R³ = 5-Ethynyl 179 R² =Cl, Z = O, R³ = 5-Ethenyl 180 R² = Cl, Z = O, R³ = 5-SO₂Me 181 R² = Cl,Z = O, R³ = 5-OAc 182 R² = Cl, Z = O, R³ = 5-c-Pr 183 R² = Cl, Z = O, R³= 5-i-Pr 184 R² = Cl, Z = O, R³ = 5-Ph 185 R² = Cl, Z = O, R³ = 6-F 186R² = Cl, Z = O, R³ = 6-Cl 187 R² = Cl, Z = O, R³ = 6-Br 188 R² = Cl, Z =O, R³ = 6-I 189 R² = Cl, Z = O, R³ = 6-CN 190 R² = Cl, Z = O, R³ = 6-NO₂191 R² = Cl, Z = O, R³ = 6-OMe 192 R² = Cl, Z = O, R³ = 6-OCF₃ 193 R² =Cl, Z = O, R³ = 6-CF₃ 194 R² = Cl, Z = O, R³ = 6-CHF₂ 195 R² = Cl, Z =O, R³ = 6-CH₂F 196 R² = Cl, Z = O, R³ = 6-CHO 197 R² = Cl, Z = O, R³ =6-Me 198 R² = Cl, Z = O, R³ = 6-Et 199 R² = Cl, Z = O, R³ = 6-Ethynyl200 R² = Cl, Z = O, R³ = 6-Ethenyl 201 R² = Cl, Z = O, R³ = 6-SO₂Me 202R² = Cl, Z = O, R³ = 6-OAc 203 R² = Cl, Z = O, R³ = 6-c-Pr 204 R² = Cl,Z = O, R³ = 6-i-Pr 205 R² = Cl, Z = O, R³ = 6-Ph 206 R² = Cl, Z = O, R³= 4,5-di-F 207 R² = Cl, Z = O, R³ = 4,5-di-Cl 208 R² = Cl, Z = O, R³ =4,5-di-Br 209 R² = Cl, Z = O, R³ = 4,5-di-CN 210 R² = Cl, Z = O, R³ =4,5-di-Me 211 R² = Cl, Z = O, R³ = 4,5-di-OMe 212 R² = Cl, Z = O, R³ =4,5-di-CF₃ 213 R² = I, Z = O, R³ = H (m = 0) 214 R² = I, Z = O, R³ = 4-F215 R² = I, Z = O, R³ = 4-Cl 216 R² = I, Z = O, R³ = 4-Br 217 R² = I, Z= O, R³ = 4-I 218 R² = I, Z = O, R³ = 4-CN 219 R² = I, Z = O, R³ = 4-NO₂220 R² = I, Z = O, R³ = 4-OMe 221 R² = I, Z = O, R³ = 4-OCF₃ 222 R² = I,Z = O, R³ = 4-CF₃ 223 R² = I, Z = O, R³ = 4-CHF₂ 224 R² = I, Z = O, R³ =4-CH₂F 225 R² = I, Z = O, R³ = 4-CHO 226 R² = I, Z = O, R³ = 4-Me 227 R²= I, Z = O, R³ = 4-Et 228 R² = I, Z = O, R³ = 4-Ethynyl 229 R² = I, Z =O, R³ = 4-Ethenyl 230 R² = I, Z = O, R³ = 4-SO₂Me 231 R² = I, Z = O, R³= 4-OAc 232 R² = I, Z = O, R³ = 4-c-Pr 233 R² = I, Z = O, R³ = 4-i-Pr234 R² = I, Z = O, R³ = 4-Ph 235 R² = I, Z = O, R³ = 5-F 236 R² = I, Z =O, R³ = 5-Cl 237 R² = I, Z = O, R³ = 5-Br 238 R² = I, Z = O, R³ = 5-I239 R² = I, Z = O, R³ = 5-CN 240 R² = I, Z = O, R³ = 5-NO₂ 241 R² = I, Z= O, R³ = 5-OMe 242 R² = I, Z = O, R³ = 5-OCF₃ 243 R² = I, Z = O, R³ =5-CF₃ 244 R² = I, Z = O, R³ = 5-CHF₂ 245 R² = I, Z = O, R³ = 5-CH₂F 246R² = I, Z = O, R³ = 5-CHO 247 R² = I, Z = O, R³ = 5-Me 248 R² = I, Z =O, R³ = 5-Et 249 R² = I, Z = O, R³ = 5-Ethynyl 250 R² = I, Z = O, R³ =5-Ethenyl 251 R² = I, Z = O, R³ = 5-SO₂Me 252 R² = I, Z = O, R³ = 5-OAc253 R² = I, Z = O, R³ = 5-c-Pr 254 R² = I, Z = O, R³ = 5-i-Pr 255 R² =I, Z = O, R³ = 5-Ph 256 R² = I, Z = O, R³ = 6-F 257 R² = I, Z = O, R³ =6-Cl 258 R² = I, Z = O, R³ = 6-Br 259 R² = I, Z = O, R³ = 6-I 260 R² =I, Z = O, R³ = 6-CN 261 R² = I, Z = O, R³ = 6-NO₂ 262 R² = I, Z = O, R³= 6-OMe 263 R² = I, Z = O, R³ = 6-OCF₃ 264 R² = I, Z = O, R³ = 6-CF₃ 265R² = I, Z = O, R³ = 6-CHF₂ 266 R² = I, Z = O, R³ = 6-CH₂F 267 R² = I, Z= O, R³ = 6-CHO 268 R² = I, Z = O, R³ = 6-Me 269 R² = I, Z = O, R³ =6-Et 270 R² = I, Z = O, R³ = 6-Ethynyl 271 R² = I, Z = O, R³ = 6-Ethenyl272 R² = I, Z = O, R³ = 6-SO₂Me 273 R² = I, Z = O, R³ = 6-OAc 274 R² =I, Z = O, R³ = 6-c-Pr 275 R² = I, Z = O, R³ = 6-i-Pr 276 R² = I, Z = O,R³ = 6-Ph 277 R² = I, Z = O, R³ = 4,5-di-F 278 R² = I, Z = O, R³ =4,5-di-Cl 279 R² = I, Z = O, R³ = 4,5-di-Br 280 R² = I, Z = O, R³ =4,5-di-CN 281 R² = I, Z = O, R³ = 4,5-di-Me 282 R² = I, Z = O, R³ =4,5-di-OMe 283 R² = I, Z = O, R³ = 4,5-di-CF₃ 284 R² = Me, Z = O, R³ =4-F 285 R² = Me, Z = O, R³ = 4-Cl 286 R² = Me, Z = O, R³ = 4-Br 287 R² =Me, Z = O, R³ = 4-I 288 R² = Me, Z = O, R³ = 4-CN 289 R² = Me, Z = O, R³= 4-NO₂ 290 R² = Me, Z = O, R³ = 4-OMe 291 R² = Me, Z = O, R³ = 4-OCF₃292 R² = Me, Z = O, R³ = 4-CF₃ 293 R² = Me, Z = O, R³ = 4-CHF₂ 294 R² =Me, Z = O, R³ = 4-CH₂F 295 R² = Me, Z = O, R³ = 4-CHO 296 R² = Me, Z =O, R³ = 4-Me 297 R² = Me, Z = O, R³ = 4-Et 298 R² = Me, Z = O, R³ =4-Ethynyl 299 R² = Me, Z = O, R³ = 4-Ethenyl 300 R² = Me, Z = O, R³ =4-SO₂Me 301 R² = Me, Z = O, R³ = 4-OAc 302 R² = Me, Z = O, R³ = 4-c-Pr303 R² = Me, Z = O, R³ = 4-i-Pr 304 R² = Me, Z = O, R³ = 4-Ph 305 R² =Me, Z = O, R³ = 5-F 306 R² = Me, Z = O, R³ = 5-Cl 307 R² = Me, Z = O, R³= 5-Br 308 R² = Me, Z = O, R³ = 5-I 309 R² = Me, Z = O, R³ = 5-CN 310 R²= Me, Z = O, R³ = 5-NO₂ 311 R² = Me, Z = O, R³ = 5-OMe 312 R² = Me, Z =O, R³ = 5-OCF₃ 313 R² = Me, Z = O, R³ = 5-CF₃ 314 R² = Me, Z = O, R³ =5-CHF₂ 315 R² = Me, Z = O, R³ = 5-CH₂F 316 R² = Me, Z = O, R³ = 5-CHO317 R² = Me, Z = O, R³ = 5-Me 318 R² = Me, Z = O, R³ = 5-Et 319 R² = Me,Z = O, R³ = 5-Ethynyl 320 R² = Me, Z = O, R³ = 5-Ethenyl 321 R² = Me, Z= O, R³ = 5-SO₂Me 322 R² = Me, Z = O, R³ = 5-OAc 323 R² = Me, Z = O, R³= 5-c-Pr 324 R² = Me, Z = O, R³ = 5-i-Pr 325 R² = Me, Z = O, R³ = 5-Ph326 R² = Me, Z = O, R³ = 6-F 327 R² = Me, Z = O, R³ = 6-Cl 328 R² = Me,Z = O, R³ = 6-Br 329 R² = Me, Z = O, R³ = 6-I 330 R² = Me, Z = O, R³ =6-CN 331 R² = Me, Z = O, R³ = 6-NO₂ 332 R² = Me, Z = O, R³ = 6-OMe 333R² = Me, Z = O, R³ = 6-OCF₃ 334 R² = Me, Z = O, R³ = 6-CF₃ 335 R² = Me,Z = O, R³ = 6-CHF₂ 336 R² = Me, Z = O, R³ = 6-CH₂F 337 R² = Me, Z = O,R³ = 6-CHO 338 R² = Me, Z = O, R³ = 6-Me 339 R² = Me, Z = O, R³ = 6-Et340 R² = Me, Z = O, R³ = 6-Ethynyl 341 R² = Me, Z = O, R³ = 6-Ethenyl342 R² = Me, Z = O, R³ = 6-SO₂Me 343 R² = Me, Z = O, R³ = 6-OAc 344 R² =Me, Z = O, R³ = 6-c-Pr 345 R² = Me, Z = O, R³ = 6-i-Pr 346 R² = Me, Z =O, R³ = 6-Ph 347 R² = Me, Z = O, R³ = 4,5-di-F 348 R² = Me, Z = O, R³ =4,5-di-Cl 349 R² = Me, Z = O, R³ = 4,5-di-Br 350 R² = Me, Z = O, R³ =4,5-di-CN 351 R² = Me, Z = O, R³ = 4,5-di-Me 352 R² = Me, Z = O, R³ =4,5-di-OMe 353 R² = Me, Z = O, R³ = 4,5-di-CF₃ 354 R² = CN, Z = O, R³ =H (m = 0) 355 R² = CN, Z = O, R³ = 4-F 356 R² = CN, Z = O, R³ = 4-Cl 357R² = CN, Z = O, R³ = 4-Br 358 R² = CN, Z = O, R³ = 4-I 359 R² = CN, Z =O, R³ = 4-CN 360 R² = CN, Z = O, R³ = 4-NO₂ 361 R² = CN, Z = O, R³ =4-OMe 362 R² = CN, Z = O, R³ = 4-OCF₃ 363 R² = CN, Z = O, R³ = 4-CF₃ 364R² = CN, Z = O, R³ = 4-CHF₂ 365 R² = CN, Z = O, R³ = 4-CH₂F 366 R² = CN,Z = O, R³ = 4-CHO 367 R² = CN, Z = O, R³ = 4-Me 368 R² = CN, Z = O, R³ =4-Et 369 R² = CN, Z = O, R³ = 4-Ethynyl 370 R² = CN, Z = O, R³ =4-Ethenyl 371 R² = CN, Z = O, R³ = 4-SO₂Me 372 R² = CN, Z = O, R³ =4-OAc 373 R² = CN, Z = O, R³ = 4-c-Pr 374 R² = CN, Z = O, R³ = 4-i-Pr375 R² = CN, Z = O, R³ = 4-Ph 376 R² = CN, Z = O, R³ = 5-F 377 R² = CN,Z = O, R³ = 5-Cl 378 R² = CN, Z = O, R³ = 5-Br 379 R² = CN, Z = O, R³ =5-I 380 R² = CN, Z = O, R³ = 5-CN 381 R² = CN, Z = O, R³ = 5-NO₂ 382 R²= CN, Z = O, R³ = 5-OMe 383 R² = CN, Z = O, R³ = 5-OCF₃ 384 R² = CN, Z =O, R³ = 5-CF₃ 385 R² = CN, Z = O, R³ = 5-CHF₂ 386 R² = CN, Z = O, R³ =5-CH₂F 387 R² = CN, Z = O, R³ = 5-CHO 388 R² = CN, Z = O, R³ = 5-Me 389R² = CN, Z = O, R³ = 5-Et 390 R² = CN, Z = O, R³ = 5-Ethynyl 391 R² =CN, Z = O, R³ = 5-Ethenyl 392 R² = CN, Z = O, R³ = 5-SO₂Me 393 R² = CN,Z = O, R³ = 5-OAc 394 R² = CN, Z = O, R³ = 5-c-Pr 395 R² = CN, Z = O, R³= 5-i-Pr 396 R² = CN, Z = O, R³ = 5-Ph 397 R² = CN, Z = O, R³ = 6-F 398R² = CN, Z = O, R³ = 6-Cl 399 R² = CN, Z = O, R³ = 6-Br 400 R² = CN, Z =O, R³ = 6-I 401 R² = CN, Z = O, R³ = 6-CN 402 R² = CN, Z = O, R³ = 6-NO₂403 R² = CN, Z = O, R³ = 6-OMe 404 R² = CN, Z = O, R³ = 6-OCF₃ 405 R² =CN, Z = O, R³ = 6-CF₃ 406 R² = CN, Z = O, R³ = 6-CHF₂ 407 R² = CN, Z =O, R³ = 6-CH₂F 408 R² = CN, Z = O, R³ = 6-CHO 409 R² = CN, Z = O, R³ =6-Me 410 R² = CN, Z = O, R³ = 6-Et 411 R² = CN, Z = O, R³ = 6-Ethynyl412 R² = CN, Z = O, R³ = 6-Ethenyl 413 R² = CN, Z = O, R³ = 6-SO₂Me 414R² = CN, Z = O, R³ = 6-OAc 415 R² = CN, Z = O, R³ = 6-c-Pr 416 R² = CN,Z = O, R³ = 6-i-Pr 417 R² = CN, Z = O, R³ = 6-Ph 418 R² = CN, Z = O, R³= 4,5-di-F 419 R² = CN, Z = O, R³ = 4,5-di-Cl 420 R² = CN, Z = O, R³ =4,5-di-Br 421 R² = CN, Z = O, R³ = 4,5-di-CN 422 R² = CN, Z = O, R³ =4,5-di-Me 423 R² = CN, Z = O, R³ = 4,5-di-OMe 424 R² = CN, Z = O, R³ =4,5-di-CF₃ 425 R² = NO₂, Z = O, R³ = H (m = 0) 426 R² = NO₂, Z = O, R³ =4-F 427 R² = NO₂, Z = O, R³ = 4-Cl 428 R² = NO₂, Z = O, R³ = 4-Br 429 R²= NO₂, Z = O, R³ = 4-I 430 R² = NO₂, Z = O, R³ = 4-CN 431 R² = NO₂, Z =O, R³ = 4-NO₂ 432 R² = NO₂, Z = O, R³ = 4-OMe 433 R² = NO₂, Z = O, R³ =4-OCF₃ 434 R² = NO₂, Z = O, R³ = 4-CF₃ 435 R² = NO₂, Z = O, R³ = 4-CHF₂436 R² = NO₂, Z = O, R³ = 4-CH₂F 437 R² = NO₂, Z = O, R³ = 4-CHO 438 R²= NO₂, Z = O, R³ = 4-Me 439 R² = NO₂, Z = O, R³ = 4-Et 440 R² = NO₂, Z =O, R³ = 4-Ethynyl 441 R² = NO₂, Z = O, R³ = 4-Ethenyl 442 R² = NO₂, Z =O, R³ = 4-SO₂Me 443 R² = NO₂, Z = O, R³ = 4-OAc 444 R² = NO₂, Z = O, R³= 4-c-Pr 445 R² = NO₂, Z = O, R³ = 4-i-Pr 446 R² = NO₂, Z = O, R³ = 4-Ph447 R² = NO₂, Z = O, R³ = 5-F 448 R² = NO₂, Z = O, R³ = 5-Cl 449 R² =NO₂, Z = O, R³ = 5-Br 450 R² = NO₂, Z = O, R³ = 5-I 451 R² = NO₂, Z = O,R³ = 5-CN 452 R² = NO₂, Z = O, R³ = 5-NO₂ 453 R² = NO₂, Z = O, R³ =5-OMe 454 R² = NO₂, Z = O, R³ = 5-OCF₃ 455 R² = NO₂, Z = O, R³ = 5-CF₃456 R² = NO₂, Z = O, R³ = 5-CHF₂ 457 R² = NO₂, Z = O, R³ = 5-CH₂F 458 R²= NO₂, Z = O, R³ = 5-CHO 459 R² = NO₂, Z = O, R³ = 5-Me 460 R² = NO₂, Z= O, R³ = 5-Et 461 R² = NO₂, Z = O, R³ = 5-Ethynyl 462 R² = NO₂, Z = O,R³ = 5-Ethenyl 463 R² = NO₂, Z = O, R³ = 5-SO₂Me 464 R² = NO₂, Z = O, R³= 5-OAc 465 R² = NO₂, Z = O, R³ = 5-c-Pr 466 R² = NO₂, Z = O, R³ =5-i-Pr 467 R² = NO₂, Z = O, R³ = 5-Ph 468 R² = NO₂, Z = O, R³ = 6-F 469R² = NO₂, Z = O, R³ = 6-Cl 470 R² = NO₂, Z = O, R³ = 6-Br 471 R² = NO₂,Z = O, R³ = 6-I 472 R² = NO₂, Z = O, R³ = 6-CN 473 R² = NO₂, Z = O, R³ =6-NO₂ 474 R² = NO₂, Z = O, R³ = 6-OMe 475 R² = NO₂, Z = O, R³ = 6-OCF₃476 R² = NO₂, Z = O, R³ = 6-CF₃ 477 R² = NO₂, Z = O, R³ = 6-CHF₂ 478 R²= NO₂, Z = O, R³ = 6-CH₂F 479 R² = NO₂, Z = O, R³ = 6-CHO 480 R² = NO₂,Z = O, R³ = 6-Me 481 R² = NO₂, Z = O, R³ = 6-Et 482 R² = NO₂, Z = O, R³= 6-Ethynyl 483 R² = NO₂, Z = O, R³ = 6-Ethenyl 484 R² = NO₂, Z = O, R³= 6-SO₂Me 485 R² = NO₂, Z = O, R³ = 6-OAc 486 R² = NO₂, Z = O, R³ =6-c-Pr 487 R² = NO₂, Z = O, R³ = 6-i-Pr 488 R² = NO₂, Z = O, R³ = 6-Ph489 R² = NO₂, Z = O, R³ = 4,5-di-F 490 R² = NO₂, Z = O, R³ = 4,5-di-Cl491 R² = NO₂, Z = O, R³ = 4,5-di-Br 492 R² = NO₂, Z = O, R³ = 4,5-di-CN493 R² = NO₂, Z = O, R³ = 4,5-di-Me 494 R² = NO₂, Z = O, R³ = 4,5-di-OMe495 R² = NO₂, Z = O, R³ = 4,5-di-CF₃ 496 R² = OMe, Z = O, R³ = H (m = 0)497 R² = OMe, Z = O, R³ = 4-F 498 R² = OMe, Z = O, R³ = 4-Cl 499 R² =OMe, Z = O, R³ = 4-Br 500 R² = OMe, Z = O, R³ = 4-I 501 R² = OMe, Z = O,R³ = 4-CN 502 R² = OMe, Z = O, R³ = 4-NO₂ 503 R² = OMe, Z = O, R³ =4-OMe 504 R² = OMe, Z = O, R³ = 4-OCF₃ 505 R² = OMe, Z = O, R³ = 4-CF₃506 R² = OMe, Z = O, R³ = 4-CHF₂ 507 R² = OMe, Z = O, R³ = 4-CH₂F 508 R²= OMe, Z = O, R³ = 4-CHO 509 R² = OMe, Z = O, R³ = 4-Me 510 R² = OMe, Z= O, R³ = 4-Et 511 R² = OMe, Z = O, R³ = 4-Ethynyl 512 R² = OMe, Z = O,R³ = 4-Ethenyl 513 R² = OMe, Z = O, R³ = 4-SO₂Me 514 R² = OMe, Z = O, R³= 4-OAc 515 R² = OMe, Z = O, R³ = 4-c-Pr 516 R² = OMe, Z = O, R³ =4-i-Pr 517 R² = OMe, Z = O, R³ = 4-Ph 518 R² = OMe, Z = O, R³ = 5-F 519R² = OMe, Z = O, R³ = 5-Cl 520 R² = OMe, Z = O, R³ = 5-Br 521 R² = OMe,Z = O, R³ = 5-I 522 R² = OMe, Z = O, R³ = 5-CN 523 R² = OMe, Z = O, R³ =5-NO₂ 524 R² = OMe, Z = O, R³ = 5-OMe 525 R² = OMe, Z = O, R³ = 5-OCF₃526 R² = OMe, Z = O, R³ = 5-CF₃ 527 R² = OMe, Z = O, R³ = 5-CHF₂ 528 R²= OMe, Z = O, R³ = 5-CH₂F 529 R² = OMe, Z = O, R³ = 5-CHO 530 R² = OMe,Z = O, R³ = 5-Me 531 R² = OMe, Z = O, R³ = 5-Et 532 R² = OMe, Z = O, R³= 5-Ethynyl 533 R² = OMe, Z = O, R³ = 5-Ethenyl 534 R² = OMe, Z = O, R³= 5-SO₂Me 535 R² = OMe, Z = O, R³ = 5-OAc 536 R² = OMe, Z = O, R³ =5-c-Pr 537 R² = OMe, Z = O, R³ = 5-i-Pr 538 R² = OMe, Z = O, R³ = 5-Ph539 R² = OMe, Z = O, R³ = 6-F 540 R² = OMe, Z = O, R³ = 6-Cl 541 R² =OMe, Z = O, R³ = 6-Br 542 R² = OMe, Z = O, R³ = 6-I 543 R² = OMe, Z = O,R³ = 6-CN 544 R² = OMe, Z = O, R³ = 6-NO₂ 545 R² = OMe, Z = O, R³ =6-OMe 546 R² = OMe, Z = O, R³ = 6-OCF₃ 547 R² = OMe, Z = O, R³ = 6-CF₃548 R² = OMe, Z = O, R³ = 6-CHF₂ 549 R² = OMe, Z = O, R³ = 6-CH₂F 550 R²= OMe, Z = O, R³ = 6-CHO 551 R² = OMe, Z = O, R³ = 6-Me 552 R² = OMe, Z= O, R³ = 6-Et 553 R² = OMe, Z = O, R³ = 6-Ethynyl 554 R² = OMe, Z = O,R³ = 6-Ethenyl 555 R² = OMe, Z = O, R³ = 6-SO₂Me 556 R² = OMe, Z = O, R³= 6-OAc 557 R² = OMe, Z = O, R³ = 6-c-Pr 558 R² = OMe, Z = O, R³ =6-i-Pr 559 R² = OMe, Z = O, R³ = 6-Ph 560 R² = OMe, Z = O, R³ = 4,5-di-F561 R² = OMe, Z = O, R³ = 4,5-di-Cl 562 R² = OMe, Z = O, R³ = 4,5-di-Br563 R² = OMe, Z = O, R³ = 4,5-di-CN 564 R² = OMe, Z = O, R³ = 4,5-di-Me565 R² = OMe, Z = O, R³ = 4,5-di-OMe 566 R² = OMe, Z = O, R³ =4,5-di-CF₃ 567 R² = CF₃, Z = O, R³ = H (m = 0) 568 R² = CF₃, Z = O, R³ =4-F 569 R² = CF₃, Z = O, R³ = 4-Cl 570 R² = CF₃, Z = O, R³ = 4-Br 571 R²= CF₃, Z = O, R³ = 4-I 572 R² = CF₃, Z = O, R³ = 4-CN 573 R² = CF₃, Z =O, R³ = 4-NO₂ 574 R² = CF₃, Z = O, R³ = 4-OMe 575 R² = CF₃, Z = O, R³ =4-OCF₃ 576 R² = CF₃, Z = O, R³ = 4-CF₃ 577 R² = CF₃, Z = O, R³ = 4-CHF₂578 R² = CF₃, Z = O, R³ = 4-CH₂F 579 R² = CF₃, Z = O, R³ = 4-CHO 580 R²= CF₃, Z = O, R³ = 4-Me 581 R² = CF₃, Z = O, R³ = 4-Et 582 R² = CF₃, Z =O, R³ = 4-Ethynyl 583 R² = CF₃, Z = O, R³ = 4-Ethenyl 584 R² = CF₃, Z =O, R³ = 4-SO₂Me 585 R² = CF₃, Z = O, R³ = 4-OAc 586 R² = CF₃, Z = O, R³= 4-c-Pr 587 R² = CF₃, Z = O, R³ = 4-i-Pr 588 R² = CF₃, Z = O, R³ = 4-Ph589 R² = CF₃, Z = O, R³ = 5-F 590 R² = CF₃, Z = O, R³ = 5-Cl 591 R² =CF₃, Z = O, R³ = 5-Br 592 R² = CF₃, Z = O, R³ = 5-I 593 R² = CF₃, Z = O,R³ = 5-CN 594 R² = CF₃, Z = O, R³ = 5-NO₂ 595 R² = CF₃, Z = O, R³ =5-OMe 596 R² = CF₃, Z = O, R³ = 5-OCF₃ 597 R² = CF₃, Z = O, R³ = 5-CF₃598 R² = CF₃, Z = O, R³ = 5-CHF₂ 599 R² = CF₃, Z = O, R³ = 5-CH₂F 600 R²= CF₃, Z = O, R³ = 5-CHO 601 R² = CF₃, Z = O, R³= 5-Me 602 R² = CF₃, Z =O, R³ = 5-Et 603 R² = CF₃, Z = O, R³ = 5-Ethynyl 604 R² = CF₃, Z = O, R³= 5-Ethenyl 605 R² = CF₃, Z = O, R³ = 5-SO₂Me 606 R² = CF₃, Z = O, R³ =5-OAc 607 R² = CF₃, Z = O, R³ = 5-c-Pr 608 R² = CF₃, Z = O, R³ = 5-i-Pr609 R² = CF₃, Z = O, R³ = 5-Ph 610 R² = CF₃, Z = O, R³ = 6-F 611 R² =CF₃, Z = O, R³ = 6-Cl 612 R² = CF₃, Z = O, R³ = 6-Br 613 R² = CF₃, Z =O, R³ = 6-I 614 R² = CF₃, Z = O, R³ = 6-CN 615 R² = CF₃, Z = O, R³ =6-NO₂ 616 R² = CF₃, Z = O, R³ = 6-OMe 617 R² = CF₃, Z = O, R³ = 6-OCF₃618 R² = CF₃, Z = O, R³ = 6-CF₃ 619 R² = CF₃, Z = O, R³ = 6-CHF₂ 620 R²= CF₃, Z = O, R³ = 6-CH₂F 621 R² = CF₃, Z = O, R³ = 6-CHO 622 R² = CF₃,Z = O, R³ = 6-Me 623 R² = CF₃, Z = O, R³ = 6-Et 624 R² = CF₃, Z = O, R³= 6-Ethynyl 625 R² = CF₃, Z = O, R³ = 6-Ethenyl 626 R² = CF₃, Z = O, R³= 6-SO₂Me 627 R² = CF₃, Z = O, R³ = 6-OAc 628 R² = CF₃, Z = O, R³ =6-c-Pr 629 R² = CF₃, Z = O, R³ = 6-i-Pr 630 R² = CF₃, Z = O, R³ = 6-Ph631 R² = CF₃, Z = O, R³ = 4,5-di-F 632 R² = CF₃, Z = O, R³ = 4,5-di-Cl633 R² = CF₃, Z = O, R³ = 4,5-di-Br 634 R² = CF₃, Z = O, R³ = 4,5-di-CN635 R² = CF₃, Z = O, R³ = 4,5-di-Me 636 R² = CF₃, Z = O, R³ = 4,5-di-OMe637 R² = CHF₂, Z = O, R³ = H (m = 0) 638 R² = CHF₂, Z = O, R³ = 4-F 639R² = CHF₂, Z = O, R³ = 4-Cl 640 R² = CHF₂, Z = O, R³ = 4-Br 641 R² =CHF₂, Z = O, R³ = 4-I 642 R² = CHF₂, Z = O, R³ = 4-CN 643 R² = CHF₂, Z =O, R³ = 4-NO₂ 644 R² = CHF₂, Z = O, R³ = 4-OMe 645 R² = CHF₂, Z = O, R³= 4-OCF₃ 646 R² = CHF₂, Z = O, R³ = 4-CF₃ 647 R² = CHF₂, Z = O, R³ =4-CHF₂ 648 R² = CHF₂, Z = O, R³ = 4-CH₂F 649 R² = CHF₂, Z = O, R³ =4-CHO 650 R² = CHF₂, Z = O, R³ = 4-Me 651 R² = CHF₂, Z = O, R³ = 4-Et652 R² = CHF₂, Z = O, R³ = 4-Ethynyl 653 R² = CHF₂, Z = O, R³ =4-Ethenyl 654 R² = CHF₂, Z = O, R³ = 4-SO₂Me 655 R² = CHF₂, Z = O, R³ =4-OAc 656 R² = CHF₂, Z = O, R³ = 4-c-Pr 657 R² = CHF₂, Z = O, R³ =4-i-Pr 658 R² = CHF₂, Z = O, R³ = 4-Ph 659 R² = CHF₂, Z = O, R³ = 5-F660 R² = CHF₂, Z = O, R³ = 5-Cl 661 R² = CHF₂, Z = O, R³ = 5-Br 662 R² =CHF₂, Z = O, R³ = 5-I 663 R² = CHF₂, Z = O, R³ = 5-CN 664 R² = CHF₂, Z =O, R³ = 5-NO₂ 665 R² = CHF₂, Z = O, R³ = 5-OMe 666 R² = CHF₂, Z = O, R³= 5-OCF₃ 667 R² = CHF₂, Z = O, R³ = 5-CF₃ 668 R² = CHF₂, Z = O, R³ =5-CHF₂ 669 R² = CHF₂, Z = O, R³ = 5-CH₂F 670 R² = CHF₂, Z = O, R³ =5-CHO 671 R² = CHF₂, Z = O, R³ = 5-Me 672 R² = CHF₂, Z = O, R³ = 5-Et673 R² = CHF₂, Z = O, R³ = 5-Ethynyl 674 R² = CHF₂, Z = O, R³ =5-Ethenyl 675 R² = CHF₂, Z = O, R³ = 5-SO₂Me 676 R² = CHF₂, Z = O, R³ =5-OAc 677 R² = CHF₂, Z = O, R³ = 5-c-Pr 678 R² = CHF₂, Z = O, R³ =5-i-Pr 679 R² = CHF₂, Z = O, R³ = 5-Ph 680 R² = CHF₂, Z = O, R³ = 6-F681 R² = CHF₂, Z = O, R³ = 6-Cl 682 R² = CHF₂, Z = O, R³ = 6-Br 683 R² =CHF₂, Z = O, R³ = 6-I 684 R² = CHF₂, Z = O, R³ = 6-CN 685 R² = CHF₂, Z =O, R³ = 6-NO₂ 686 R² = CHF₂, Z = O, R³ = 6-OMe 687 R² = CHF₂, Z = O, R³= 6-OCF₃ 688 R² = CHF₂, Z = O, R³ = 6-CF₃ 689 R² = CHF₂, Z = O, R³ =6-CHF₂ 690 R² = CHF₂, Z = O, R³ = 6-CH₂F 691 R² = CHF₂, Z = O, R³ =6-CHO 692 R² = CHF₂, Z = O, R³ = 6-Me 693 R² = CHF₂, Z = O, R³ = 6-Et694 R² = CHF₂, Z = O, R³ = 6-Ethynyl 695 R² = CHF₂, Z = O, R³ =6-Ethenyl 696 R² = CHF₂, Z = O, R³ = 6-SO₂Me 697 R² = CHF₂, Z = O, R³ =6-OAc 698 R² = CHF₂, Z = O, R³ = 6-c-Pr 699 R² = CHF₂, Z = O, R³ =6-i-Pr 700 R² = CHF₂, Z = O, R³ = 6-Ph 701 R² = CHF₂, Z = O, R³ =4,5-di-F 702 R² = CHF₂, Z = O, R³ = 4,5-di-Cl 703 R² = CHF₂, Z = O, R³ =4,5-di-Br 704 R² = CHF₂, Z = O, R³ = 4,5-di-CN 705 R² = CHF₂, Z = O, R³= 4,5-di-Me 706 R² = CHF₂, Z = O, R³ = 4,5-di-OMe 707 R² = CHF₂, Z = O,R³ = 4,5-di-CF₃ 708 R² = SO₂Me, Z = O, R³ = H (m = 0) 709 R² = SO₂Me, Z= O, R³ = 4-F 710 R² = SO₂Me, Z = O, R³ = 4-Cl 711 R² = SO₂Me, Z = O, R³= 4-Br 712 R² = SO₂Me, Z = O, R³ = 4-I 713 R² = SO₂Me, Z = O, R³ = 4-CN714 R² = SO₂Me, Z = O, R³ = 4-NO₂ 715 R² = SO₂Me, Z = O, R³ = 4-OMe 716R² = SO₂Me, Z = O, R³ = 4-OCF₃ 717 R² = SO₂Me, Z = O, R³ = 4-CF₃ 718 R²= SO₂Me, Z = O, R³ = 4-CHF₂ 719 R² = SO₂Me, Z = O, R³ = 4-CH₂F 720 R² =SO₂Me, Z = O, R³ = 4-CHO 721 R² = SO₂Me, Z = O, R³ = 4-Me 722 R² =SO₂Me, Z = O, R³ = 4-Et 723 R² = SO₂Me, Z = O, R³ = 4-Ethynyl 724 R² =SO₂Me, Z = O, R³ = 4-Ethenyl 725 R² = SO₂Me, Z = O, R³ = 4-SO₂Me 726 R²= SO₂Me, Z = O, R³ = 4-OAc 727 R² = SO₂Me, Z = O, R³ = 4-c-Pr 728 R² =SO₂Me, Z = O, R³ = 4-i-Pr 729 R² = SO₂Me, Z = O, R³ = 4-Ph 730 R² =SO₂Me, Z = O, R³ = 5-F 731 R² = SO₂Me, Z = O, R³ = 5-Cl 732 R² = SO₂Me,Z = O, R³ = 5-Br 733 R² = SO₂Me, Z = O, R³ = 5-I 734 R² = SO₂Me, Z = O,R³ = 5-CN 735 R² = SO₂Me, Z = O, R³ = 5-NO₂ 736 R² = SO₂Me, Z = O, R³ =5-OMe 737 R² = SO₂Me, Z = O, R³ = 5-OCF₃ 738 R² = SO₂Me, Z = O, R³ =5-CF₃ 739 R² = SO₂Me, Z = O, R³ = 5-CHF₂ 740 R² = SO₂Me, Z = O, R³ =5-CH₂F 741 R² = SO₂Me, Z = O, R³ = 5-CHO 742 R² = SO₂Me, Z = O, R³ =5-Me 743 R² = SO₂Me, Z = O, R³ = 5-Et 744 R² = SO₂Me, Z = O, R³ =5-Ethynyl 745 R² = SO₂Me, Z = O, R³ = 5-Ethenyl 746 R² = SO₂Me, Z = O,R³ = 5-SO₂Me 747 R² = SO₂Me, Z = O, R³ = 5-OAc 748 R² = SO₂Me, Z = O, R³= 5-c-Pr 749 R² = SO₂Me, Z = O, R³ = 5-i-Pr 750 R² = SO₂Me, Z = O, R³ =5-Ph 751 R² = SO₂Me, Z = O, R³ = 6-F 752 R² = SO₂Me, Z = O, R³ = 6-Cl753 R² = SO₂Me, Z = O, R³ = 6-Br 754 R² = SO₂Me, Z = O, R³ = 6-I 755 R²= SO₂Me, Z = O, R³ = 6-CN 756 R² = SO₂Me, Z = O, R³ = 6-NO₂ 757 R² =SO₂Me, Z = O, R³ = 6-OMe 758 R² = SO₂Me, Z = O, R³ = 6-OCF₃ 759 R² =SO₂Me, Z = O, R³ = 6-CF₃ 760 R² = SO₂Me, Z = O, R³ = 6-CHF₂ 761 R² =SO₂Me, Z = O, R³ = 6-CH₂F 762 R² = SO₂Me, Z = O, R³ = 6-CHO 763 R² =SO₂Me, Z = O, R³ = 6-Me 764 R² = SO₂Me, Z = O, R³ = 6-Et 765 R² = SO₂Me,Z = O, R³ = 6-Ethynyl 766 R² = SO₂Me, Z = O, R³ = 6-Ethenyl 767 R² =SO₂Me, Z = O, R³ = 6-SO₂Me 768 R² = SO₂Me, Z = O, R³ = 6-OAc 769 R² =SO₂Me, Z = O, R³ = 6-c-Pr 770 R² = SO₂Me, Z = O, R³ = 6-i-Pr 771 R² =SO₂Me, Z = O, R³ = 6-Ph 772 R² = SO₂Me, Z = O, R³ = 4,5-di-F 773 R² =SO₂Me, Z = O, R³ = 4,5-di-Cl 774 R² = SO₂Me, Z = O, R³ = 4,5-di-Br 775R² = SO₂Me, Z = O, R³ = 4,5-di-CN 776 R² = SO₂Me, Z = O, R³ = 4,5-di-Me777 R² = SO₂Me, Z = O, R³ = 4,5-di-OMe 778 R² = SO₂Me, Z = O, R³ =4,5-di-CF₃

A compound of this invention will generally be used as a herbicidalactive ingredient in a composition, i.e. formulation, with at least oneadditional component selected from the group consisting of surfactants,solid diluents and liquid diluents, which serves as a carrier. Theformulation or composition ingredients are selected to be consistentwith the physical properties of the active ingredient, mode ofapplication and environmental factors such as soil type, moisture andtemperature.

Useful formulations include both liquid and solid compositions. Liquidcompositions include solutions (including emulsifiable concentrates),suspensions, emulsions (including microemulsions, oil-in-wateremulsions, flowable concentrates and/or suspoemulsions) and the like,which optionally can be thickened into gels. The general types ofaqueous liquid compositions are soluble concentrate, suspensionconcentrate, capsule suspension, concentrated emulsion, microemulsion,oil-in-water emulsion, flowable concentrate and suspo-emulsion. Thegeneral types of nonaqueous liquid compositions are emulsifiableconcentrate, microemulsifiable concentrate, dispersible concentrate andoil dispersion.

The general types of solid compositions are dusts, powders, granules,pellets, prills, pastilles, tablets, filled films (including seedcoatings) and the like, which can be water-dispersible (“wettable”) orwater-soluble. Films and coatings formed from film-forming solutions orflowable suspensions are particularly useful for seed treatment. Activeingredient can be (micro)encapsulated and further formed into asuspension or solid formulation; alternatively the entire formulation ofactive ingredient can be encapsulated (or “overcoated”). Encapsulationcan control or delay release of the active ingredient. An emulsifiablegranule combines the advantages of both an emulsifiable concentrateformulation and a dry granular formulation. High-strength compositionsare primarily used as intermediates for further formulation.

Sprayable formulations are typically extended in a suitable mediumbefore spraying. Such liquid and solid formulations are formulated to bereadily diluted in the spray medium, usually water, but occasionallyanother suitable medium like an aromatic or paraffinic hydrocarbon orvegetable oil. Spray volumes can range from about from about one toseveral thousand liters per hectare, but more typically are in the rangefrom about ten to several hundred liters per hectare. Sprayableformulations can be tank mixed with water or another suitable medium forfoliar treatment by aerial or ground application, or for application tothe growing medium of the plant. Liquid and dry formulations can bemetered directly into drip irrigation systems or metered into the furrowduring planting.

The formulations will typically contain effective amounts of activeingredient, diluent and surfactant within the following approximateranges which add up to 100 percent by weight.

Weight Percent Active Sur- Ingredient Diluent factant Water-Dispersibleand Water-soluble 0.001-90 0-99.999 0-15 Granules, Tablets and PowdersOil Dispersions, Suspensions,    1-50 40-99    0-50 Emulsions, Solutions(including Emulsifiable Concentrates) Dusts    1-25 70-99    0-5 Granules and Pellets 0.001-99 5-99.999 0-15 High Strength Compositions  90-99 0-10    0-2 

Solid diluents include, for example, clays such as bentonite,montmorillonite, attapulgite and kaolin, gypsum, cellulose, titaniumdioxide, zinc oxide, starch, dextrin, sugars (e.g., lactose, sucrose),silica, talc, mica, diatomaceous earth, urea, calcium carbonate, sodiumcarbonate and bicarbonate, and sodium sulfate. Typical solid diluentsare described in Watkins et al., Handbook of Insecticide Dust Diluentsand Carriers, 2nd Ed., Dorland Books, Caldwell, N.J.

Liquid diluents include, for example, water, N,N-dimethylalkanamides(e.g., N,N-dimethylformamide), limonene, dimethyl sulfoxide,N-alkylpyrrolidones (e.g., N-methylpyrrolidinone), alkyl phosphates(e.g., triethyl phosphate), ethylene glycol, triethylene glycol,propylene glycol, dipropylene glycol, polypropylene glycol, propylenecarbonate, butylene carbonate, paraffins (e.g., white mineral oils,normal paraffins, isoparaffins), alkylbenzenes, alkylnaphthalenes,glycerine, glycerol triacetate, sorbitol, aromatic hydrocarbons,dearomatized aliphatics, alkylbenzenes, alkylnaphthalenes, ketones suchas cyclohexanone, 2-heptanone, isophorone and4-hydroxy-4-methyl-2-pentanone, acetates such as isoamyl acetate, hexylacetate, heptyl acetate, octyl acetate, nonyl acetate, tridecyl acetateand isobornyl acetate, other esters such as alkylated lactate esters,dibasic esters, alkyl and aryl benzoates and γ-butyrolactone, andalcohols, which can be linear, branched, saturated or unsaturated, suchas methanol, ethanol, n-propanol, isopropyl alcohol, n-butanol, isobutylalcohol, n-hexanol, 2-ethylhexanol, n-octanol, decanol, isodecylalcohol, isooctadecanol, cetyl alcohol, lauryl alcohol, tridecylalcohol, oleyl alcohol, cyclohexanol, tetrahydrofurfuryl alcohol,diacetone alcohol, cresol and benzyl alcohol. Liquid diluents alsoinclude glycerol esters of saturated and unsaturated fatty acids(typically C₆-C₂₂), such as plant seed and fruit oils (e.g., oils ofolive, castor, linseed, sesame, corn (maize), peanut, sunflower,grapeseed, safflower, cottonseed, soybean, rapeseed, coconut and palmkernel), animal-sourced fats (e.g., beef tallow, pork tallow, lard, codliver oil, fish oil), and mixtures thereof. Liquid diluents also includealkylated fatty acids (e.g., methylated, ethylated, butylated) whereinthe fatty acids may be obtained by hydrolysis of glycerol esters fromplant and animal sources, and can be purified by distillation. Typicalliquid diluents are described in Marsden, Solvents Guide, 2nd Ed.,Interscience, New York, 1950.

The solid and liquid compositions of the present invention often includeone or more surfactants. When added to a liquid, surfactants (also knownas “surface-active agents”) generally modify, most often reduce, thesurface tension of the liquid. Depending on the nature of thehydrophilic and lipophilic groups in a surfactant molecule, surfactantscan be useful as wetting agents, dispersants, emulsifiers or defoamingagents.

Surfactants can be classified as nonionic, anionic or cationic. Nonionicsurfactants useful for the present compositions include, but are notlimited to: alcohol alkoxylates such as alcohol alkoxylates based onnatural and synthetic alcohols (which may be branched or linear) andprepared from the alcohols and ethylene oxide, propylene oxide, butyleneoxide or mixtures thereof; amine ethoxylates, alkanolamides andethoxylated alkanolamides; alkoxylated triglycerides such as ethoxylatedsoybean, castor and rapeseed oils; alkylphenol alkoxylates such asoctylphenol ethoxylates, nonylphenol ethoxylates, dinonyl phenolethoxylates and dodecyl phenol ethoxylates (prepared from the phenolsand ethylene oxide, propylene oxide, butylene oxide or mixturesthereof); block polymers prepared from ethylene oxide or propylene oxideand reverse block polymers where the terminal blocks are prepared frompropylene oxide; ethoxylated fatty acids; ethoxylated fatty esters andoils; ethoxylated methyl esters; ethoxylated tristyrylphenol (includingthose prepared from ethylene oxide, propylene oxide, butylene oxide ormixtures thereof); fatty acid esters, glycerol esters, lanolin-basedderivatives, polyethoxylate esters such as polyethoxylated sorbitanfatty acid esters, polyethoxylated sorbitol fatty acid esters andpolyethoxylated glycerol fatty acid esters; other sorbitan derivativessuch as sorbitan esters; polymeric surfactants such as randomcopolymers, block copolymers, alkyd peg (polyethylene glycol) resins,graft or comb polymers and star polymers; polyethylene glycols (pegs);polyethylene glycol fatty acid esters; silicone-based surfactants; andsugar-derivatives such as sucrose esters, alkyl polyglycosides and alkylpolysaccharides.

Useful anionic surfactants include, but are not limited to: alkylarylsulfonic acids and their salts; carboxylated alcohol or alkylphenolethoxylates; diphenyl sulfonate derivatives; lignin and ligninderivatives such as lignosulfonates; maleic or succinic acids or theiranhydrides; olefin sulfonates; phosphate esters such as phosphate estersof alcohol alkoxylates, phosphate esters of alkylphenol alkoxylates andphosphate esters of styryl phenol ethoxylates; protein-basedsurfactants; sarcosine derivatives; styryl phenol ether sulfate;sulfates and sulfonates of oils and fatty acids; sulfates and sulfonatesof ethoxylated alkylphenols; sulfates of alcohols; sulfates ofethoxylated alcohols; sulfonates of amines and amides such asN,N-alkyltaurates; sulfonates of benzene, cumene, toluene, xylene, anddodecyl and tridecylbenzenes; sulfonates of condensed naphthalenes;sulfonates of naphthalene and alkyl naphthalene; sulfonates offractionated petroleum; sulfosuccinamates; and sulfosuccinates and theirderivatives such as dialkyl sulfosuccinate salts.

Useful cationic surfactants include, but are not limited to: amides andethoxylated amides; amines such as N-alkyl propanediamines,tripropylenetriamines and dipropylenetetramines, and ethoxylated amines,ethoxylated diamines and propoxylated amines (prepared from the aminesand ethylene oxide, propylene oxide, butylene oxide or mixturesthereof); amine salts such as amine acetates and diamine salts;quaternary ammonium salts such as quaternary salts, ethoxylatedquaternary salts and diquaternary salts; and amine oxides such asalkyldimethylamine oxides and bis-(2-hydroxyethyl)-alkylamine oxides.

Also useful for the present compositions are mixtures of nonionic andanionic surfactants or mixtures of nonionic and cationic surfactants.Nonionic, anionic and cationic surfactants and their recommended usesare disclosed in a variety of published references includingMcCutcheon's Emulsifiers and Detergents, annual American andInternational Editions published by McCutcheon's Division, TheManufacturing Confectioner Publishing Co.; Sisely and Wood, Encyclopediaof Surface Active Agents, Chemical Publ. Co., Inc., New York, 1964; andA. S. Davidson and B. Milwidsky, Synthetic Detergents, Seventh Edition,John Wiley and Sons, New York, 1987.

Compositions of this invention may also contain formulation auxiliariesand additives, known to those skilled in the art as formulation aids(some of which may be considered to also function as solid diluents,liquid diluents or surfactants). Such formulation auxiliaries andadditives may control: pH (buffers), foaming during processing(antifoams such polyorganosiloxanes), sedimentation of activeingredients (suspending agents), viscosity (thixotropic thickeners),in-container microbial growth (antimicrobials), product freezing(antifreezes), color (dyes/pigment dispersions), wash-off (film formersor stickers), evaporation (evaporation retardants), and otherformulation attributes. Film formers include, for example, polyvinylacetates, polyvinyl acetate copolymers, polyvinylpyrrolidone-vinylacetate copolymer, polyvinyl alcohols, polyvinyl alcohol copolymers andwaxes. Examples of formulation auxiliaries and additives include thoselisted in McCutcheon's Volume 2: Functional Materials, annualInternational and North American editions published by McCutcheon'sDivision, The Manufacturing Confectioner Publishing Co.; and PCTPublication WO 03/024222.

The compound of Formula 1 and any other active ingredients are typicallyincorporated into the present compositions by dissolving the activeingredient in a solvent or by grinding in a liquid or dry diluent.Solutions, including emulsifiable concentrates, can be prepared bysimply mixing the ingredients. If the solvent of a liquid compositionintended for use as an emulsifiable concentrate is water-immiscible, anemulsifier is typically added to emulsify the active-containing solventupon dilution with water. Active ingredient slurries, with particlediameters of up to 2,000 μm can be wet milled using media mills toobtain particles with average diameters below 3 μm. Aqueous slurries canbe made into finished suspension concentrates (see, for example, U.S.Pat. No. 3,060,084) or further processed by spray drying to formwater-dispersible granules. Dry formulations usually require dry millingprocesses, which produce average particle diameters in the 2 to 10 μmrange. Dusts and powders can be prepared by blending and usuallygrinding (such as with a hammer mill or fluid-energy mill). Granules andpellets can be prepared by spraying the active material upon preformedgranular carriers or by agglomeration techniques. See Browning,“Agglomeration”, Chemical Engineering, Dec. 4, 1967, pp 147-48, Perry'sChemical Engineer's Handbook, 4th Ed., McGraw-Hill, New York, 1963,pages 8-57 and following, and WO 91/13546. Pellets can be prepared asdescribed in U.S. Pat. No. 4,172,714. Water-dispersible andwater-soluble granules can be prepared as taught in U.S. Pat. Nos.4,144,050, 3,920,442 and DE 3,246,493. Tablets can be prepared as taughtin U.S. Pat. Nos. 5,180,587, 5,232,701 and 5,208,030. Films can beprepared as taught in GB 2,095,558 and U.S. Pat. No. 3,299,566.

For further information regarding the art of formulation, see T. S.Woods, “The Formulator's Toolbox—Product Forms for Modern Agriculture”in Pesticide Chemistry and Bioscience, The Food-Environment Challenge,T. Brooks and T. R. Roberts, Eds., Proceedings of the 9th InternationalCongress on Pesticide Chemistry, The Royal Society of Chemistry,Cambridge, 1999, pp. 120-133. See also U.S. Pat. No. 3,235,361, Col. 6,line 16 through Col. 7, line 19 and Examples 10-41; U.S. Pat. No.3,309,192, Col. 5, line 43 through Col. 7, line 62 and Examples 8, 12,15, 39, 41, 52, 53, 58, 132, 138-140, 162-164, 166, 167 and 169-182;U.S. Pat. No. 2,891,855, Col. 3, line 66 through Col. 5, line 17 andExamples 1-4; Klingman, Weed Control as a Science, John Wiley and Sons,Inc., New York, 1961, pp 81-96; Hance et al., Weed Control Handbook, 8thEd., Blackwell Scientific Publications, Oxford, 1989; and Developmentsin formulation technology, PJB Publications, Richmond, UK, 2000.

In the following Examples, all percentages are by weight and allformulations are prepared in conventional ways. Compound numbers referto compounds in Index Tables A-B. Without further elaboration, it isbelieved that one skilled in the art using the preceding description canutilize the present invention to its fullest extent. The followingExamples are, therefore, to be construed as merely illustrative, and notlimiting of the disclosure in any way whatsoever. Percentages are byweight except where otherwise indicated.

Example A

High Strength Concentrate

Compound 1 98.5% silica aerogel 0.5% synthetic amorphous fine silica1.0%

Example B

Wettable Powder

Compound 1 65.0% dodecylphenol polyethylene glycol ether 2.0% sodiumligninsulfonate 4.0% sodium silicoaluminate 6.0% montmorillonite(calcined) 23.0%

Example C

(i) Granule

Compound 1 10.0% attapulgite granules (low volatile matter, 0.71/0.30mm; 90.0% U.S.S. No. 25-50 sieves)

Example D

Extruded Pellet

Compound 1 25.0% anhydrous sodium sulfate 10.0% crude calciumligninsulfonate 5.0% sodium alkylnaphthalenesulfonate 1.0%calcium/magnesium bentonite 59.0%

Example E

Emulsifiable Concentrate

Compound 1 10.0% polyoxyethylene sorbitol hexoleate 20.0% C₆-C₁₀ fattyacid methyl ester 70.0%

Example F

Microemulsion

Compound 1 5.0% polyvinylpyrrolidone-vinyl acetate copolymer 30.0%alkylpolyglycoside 30.0% glyceryl monooleate 15.0% water 20.0%

Example G

Suspension Concentrate

Compound 1  35% butyl polyoxyethylene/polypropylene block copolymer 4.0%stearic acid/polyethylene glycol copolymer 1.0% styrene acrylic polymer1.0% xanthan gum 0.1% propylene glycol 5.0% silicone based defoamer 0.1%1,2-benzisothiazolin-3-one 0.1% Water 53.7% 

Example H

Emulsion in Water

Compound 1 10.0% butyl polyoxyethylene/polypropylene block copolymer4.0% stearic acid/polyethylene glycol copolymer 1.0% styrene acrylicpolymer 1.0% xanthan gum 0.1% propylene glycol 5.0% silicone baseddefoamer 0.1% 1,2-benzisothiazolin-3-one 0.1% aromatic petroleum basedhydrocarbon 20.0 Water 58.7%

Example I

Oil Dispersion

Compound 1 25% polyoxyethylene sorbitol hexaoleate 15% organicallymodified bentonite clay 2.5%  fatty acid methyl ester 57.5% 

The present disclosure also includes Examples A through I above except“Compound 1” is separately replaced with “Compound 2”, “Compound 3”,“Compound 4”, “Compound 5”, “Compound 6”, “Compound 7”, “Compound 8”,“Compound 9”, “Compound 10”, “Compound 11”, “Compound 12”, “Compound 13”and “Compound 14”.

Test results indicate that the compounds of the present invention arehighly active preemergent and/or postemergent herbicides and/or plantgrowth regulants. The compounds of the inention generally show highestactivity for postemergence weed control (i.e. applied after weedseedlings emerge from the soil) and preemergence weed control (i.e.applied before weed seedlings emerge from the soil). Many of them haveutility for broad-spectrum pre- and/or postemergence weed control inareas where complete control of all vegetation is desired such as aroundfuel storage tanks, industrial storage areas, parking lots, drive-intheaters, air fields, river banks, irrigation and other waterways,around billboards and highway and railroad structures. Many of thecompounds of this invention, by virtue of selective metabolism in cropsversus weeds, or by selective activity at the locus of physiologicalinhibition in crops and weeds, or by selective placement on or withinthe environment of a mixture of crops and weeds, are useful for theselective control of grass and broadleaf weeds within a crop/weedmixture. One skilled in the art will recognize that the preferredcombination of these selectivity factors within a compound or group ofcompounds can readily be determined by performing routine biologicaland/or biochemical assays. Compounds of this invention may showtolerance to important agronomic crops including, but is not limited to,alfalfa, barley, cotton, wheat, rape, sugar beets, corn (maize),sorghum, soybeans, rice, oats, peanuts, vegetables, tomato, potato,perennial plantation crops including coffee, cocoa, oil palm, rubber,sugarcane, citrus, grapes, fruit trees, nut trees, banana, plantain,pineapple, hops, tea and forests such as eucalyptus and conifers (e.g.,loblolly pine), and turf species (e.g., Kentucky bluegrass, St.Augustine grass, Kentucky fescue and Bermuda grass). Compounds of thisinvention can be used in crops genetically transformed or bred toincorporate resistance to herbicides, express proteins toxic toinvertebrate pests (such as Bacillus thuringiensis toxin), and/orexpress other useful traits. Those skilled in the art will appreciatethat not all compounds are equally effective against all weeds.Alternatively, the subject compounds are useful to modify plant growth.

As the compounds of the invention have preemergent and postemergentherbicidal activity, to control undesired vegetation by killing orinjuring the vegetation or reducing its growth, the compounds can beusefully applied by a variety of methods involving contacting aherbicidally effective amount of a compound of the invention, or acomposition comprising said compound and at least one of a surfactant, asolid diluent or a liquid diluent, to the foliage or other part of theundesired vegetation or to the environment of the undesired vegetationsuch as the soil or water in which the undesired vegetation is growingor which surrounds the seed or other propagule of the undesiredvegetation.

A herbicidally effective amount of the compounds of this invention isdetermined by a number of factors. These factors include: formulationselected, method of application, amount and type of vegetation present,growing conditions, etc. In general, a herbicidally effective amount ofcompounds of this invention is about 0.001 to 20 kg/ha with a preferredrange of about 0.004 to 1 kg/ha. One skilled in the art can easilydetermine the herbicidally effective amount necessary for the desiredlevel of weed control.

In one common embodiment, a compound of the invention is applied,typically in a formulated composition, to a locus comprising desiredvegetation (e.g., crops) and undesired vegetation (i.e. weeds), both ofwhich may be seeds, seedlings and/or larger plants, in contact with agrowth medium (e.g., soil). In this locus, a composition comprising acompound of the invention can be directly applied to a plant or a partthereof, particularly of the undesired vegetation, and/or to the growthmedium in contact with the plant.

Plant varieties and cultivars of the desired vegetation in the locustreated with a compound of the invention can be obtained by conventionalpropagation and breeding methods or by genetic engineering methods.Genetically modified plants (transgenic plants) are those in which aheterologous gene (transgene) has been stably integrated into theplant's genome. A transgene that is defined by its particular locationin the plant genome is called a transformation or transgenic event.

Genetically modified plant cultivars in the locus which can be treatedaccording to the invention include those that are resistant against oneor more biotic stresses (pests such as nematodes, insects, mites, fungi,etc.) or abiotic stresses (drought, cold temperature, soil salinity,etc.), or that contain other desirable characteristics. Plants can begenetically modified to exhibit traits of, for example, herbicidetolerance, insect-resistance, modified oil profiles or droughttolerance. Useful genetically modified plants containing single genetransformation events or combinations of transformation events arelisted in Exhibit C. Additional information for the geneticmodifications listed in Exhibit C can be obtained from publiclyavailable databases maintained, for example, by the U.S. Department ofAgriculture.

The following abbreviations, T1 through T37, are used in Exhibit C fortraits. A “-” means the entry is not available; “tol.” means “tolerance”and “res.” means resistance.

Trait Description T1 Glyphosate tol. T2 High lauric acid oil T3Glufosinate tol. T4 Phytate breakdown T5 Oxynil tol. T6 Disease res. T7Insect res. T9 Modified flower color T11 ALS Herbicide tol. T12 Dicambatol. T13 Anti-allergy T14 Salt tol. T15 Cold tol. T16 Imidazolinoneherb. tol. T17 Modified alpha-amylase T18 Pollination control T19 2,4-Dtol. T20 Increased lysine T21 Drought tol. T22 Delayedripening/senescence T23 Modified product quality T24 High cellulose T25Modified starch/carbohydrate T26 Insect & disease resist. T27 Hightryptophan T28 Erect leaves semidwarf T29 Semidwarf T30 Low iron tol.T31 Modified oil/fatty acid T32 HPPD tol. T33 High oil T34Aryloxyalkanoate tol. T35 Mesotrione tol. T36 Reduced nicotine T37Modified product

Exhibit C

Crop Event Name Event Code Trait(s) Gene(s) Alfalfa J101 MON-00101-8 T1cp4 epsps (aroA:CP4) Alfalfa J163 MON-ØØ163-7 T1 cp4 epsps (aroA:CP4)Canola* 23-18-17 (Event 18) CGN-89465-2 T2 te Canola* 23-198 (Event 23)CGN-89465-2 T2 te Canola* 61061 DP-Ø61Ø61-7 T1 gat4621 Canola* 73496DP-Ø73496-4 T1 gat4621 Canola* GT200 (RT200) MON-89249-2 T1 cp4 epsps(aroA:CP4); goxv247 Canola* GT73 (RT73) MON-ØØØ73-7 T1 cp4 epsps(aroA:CP4); goxv247 Canola* HCN10 (Topas 19/2) — T3 bar Canola* HCN28(T45) ACS-BNØØ8-2 T3 pat (syn) Canola* HCN92 (Topas 19/2) ACS-BNØØ7-1 T3bar Canola* MON88302 MON-883Ø2-9 T1 cp4 epsps (aroA:CP4) Canola* MPS961— T4 phyA Canola* MPS962 — T4 phyA Canola* MPS963 — T4 phyA Canola*MPS964 — T4 phyA Canola* MPS965 — T4 phyA Canola* MS1 (B91-4)ACS-BNØØ4-7 T3 bar Canola* MS8 ACS-BNØØ5-8 T3 bar Canola* OXY-235ACS-BNØ11-5 T5 bxn Canola* PHY14 — T3 bar Canola* PHY23 — T3 bar Canola*PHY35 — T3 bar Canola* PHY36 — T3 bar Canola* RF1 (B93-101) ACS-BNØØ1-4T3 bar Canola* RF2 (B94-2) ACS-BNØØ2-5 T3 bar Canola* RF3 ACS-BNØØ3-6 T3bar Bean EMBRAPA 5.1 EMB-PV051-1 T6 ac1 (sense and antisense) Brinjal #EE-1 — T7 cry1Ac Cotton 19-51a DD-Ø1951A-7 T11 S4-HrA Cotton 281-24-236DAS-24236-5 T3, T7 pat (syn); cry1F Cotton 3006-210-23 DAS-21Ø23-5 T3,T7 pat (syn); cry1Ac Cotton 31707 — T5, T7 bxn; cry1Ac Cotton 31803 —T5, T7 bxn; cry1Ac Cotton 31807 — T5, T7 bxn; cry1Ac Cotton 31808 — T5,T7 bxn; cry1Ac Cotton 42317 — T5, T7 bxn; cry1Ac Cotton BNLA-601 — T7cry1Ac Cotton BXN10211 BXN10211-9 T5 bxn; cry1Ac Cotton BXN10215BXN10215-4 T5 bxn; cry1Ac Cotton BXN10222 BXN10222-2 T5 bxn; cry1AcCotton BXN10224 BXN10224-4 T5 bxn; cry1Ac Cotton COT102 SYN-IR102-7 T7vip3A(a) Cotton COT67B SYN-IR67B-1 T7 cry1Ab Cotton COT202 — T7 vip3ACotton Event 1 — T7 cry1Ac Cotton GMF Cry1A GTL-GMF311-7 T7 cry1Ab-AcCotton GHB119 BCS-GH005-8 T7 cry2Ae Cotton GHB614 BCS-GH002-5 T1 2mepspsCotton GK12 — T7 cry1Ab-Ac Cotton LLCotton25 ACS-GH001-3 T3 bar CottonMLS 9124 — T7 cry1C Cotton MON1076 MON-89924-2 T7 cry1Ac Cotton MON1445MON-01445-2 T1 cp4 epsps (aroA:CP4) Cotton MON15985 MON-15985-7 T7cry1Ac; cry2Ab2 Cotton MON1698 MON-89383-1 T7 cp4 epsps (aroA:CP4)Cotton MON531 MON-00531-6 T7 cry1Ac Cotton MON757 MON-00757-7 T7 cry1AcCotton MON88913 MON-88913-8 T1 cp4 epsps (aroA:CP4) Cotton Nqwe Chi 6 Bt— T7 — Cotton SKG321 — T7 cry1A; CpTI Cotton T303-3 BCS-GH003-6 T3, T7cry1Ab; bar Cotton T304-40 BCS-GH004-7 T3, T7 cry1Ab; bar CottonCE43-67B — T7 cry1Ab Cotton CE46-02A — T7 cry1Ab Cotton CE44-69D — T7cry1Ab Cotton 1143-14A — T7 cry1Ab Cotton 1143-51B — T7 cry1Ab CottonT342-142 — T7 cry1Ab Cotton PV-GHGT07 (1445) — T1 cp4 epsps (aroA:CP4)Cotton EE-GH3 — T1 mepsps Cotton EE-GH5 — T7 cry1Ab Cotton MON88701MON-88701-3 T3, T12 Modified dmo; bar Cotton OsCrl1 — T13 Modified Cry jFlax FP967 CDC-FL001-2 T11 als Lentil RH44 — T16 als Maize 3272SYN-E3272-5 T17 amy797E Maize 5307 SYN-05307-1 T7 ecry3.1Ab Maize 59122DAS-59122-7 T3, T7 cry34Ab1; cry35Ab1; pat Maize 676 PH-000676-7 T3, T18pat; dam Maize 678 PH-000678-9 T3, T18 pat; dam Maize 680 PH-000680-2T3, T18 pat; dam Maize 98140 DP-098140-6 T1, T11 gat4621; zm-hra MaizeBt10 — T3, T7 cry1Ab; pat Maize Bt176 (176) SYN-EV176-9 T3, T7 cry1Ab;bar Maize BVLA430101 — T4 phyA2 Maize CBH-351 ACS-ZM004-3 T3, T7 cry9C;bar Maize DAS40278-9 DAS40278-9 T19 aad-1 Maize DBT418 DKB-89614-9 T3,T7 cry1Ac; pinII; bar Maize DLL25 (B16) DKB-89790-5 T3 bar Maize GA21MON-00021-9 T1 mepsps Maize GG25 — T1 mepsps Maize GJ11 — T1 mepspsMaize Fl117 — T1 mepsps Maize GAT-ZM1 — T3 pat Maize LY038 REN-00038-3T20 cordapA Maize MIR162 SYN-IR162-4 T7 vip3Aa20 Maize MIR604SYN-IR604-5 T7 mcry3A Maize MON801 (MON80100) MON801 T1, T7 cry1Ab; cp4epsps (aroA:CP4); goxv247 Maize MON802 MON-80200-7 T1, T7 cry1Ab; cp4epsps (aroA:CP4); goxv247 Maize MON809 PH-MON-809-2 T1, T7 cry1Ab; cp4epsps (aroA:CP4); goxv247 Maize MON810 MON-00810-6 T1, T7 cry1Ab; cp4epsps (aroA:CP4); goxv247 Maize MON832 — T1 cp4 epsps (aroA:CP4);goxv247 Maize MON863 MON-00863-5 T7 cry3Bb1 Maize MON87427 MON-87427-7T1 cp4 epsps (aroA:CP4) Maize MON87460 MON-87460-4 T21 cspB MaizeMON88017 MON-88017-3 T1, T7 cry3Bb1; cp4 epsps (aroA:CP4) Maize MON89034MON-89034-3 T7 cry2Ab2; cry1A.105 Maize MS3 ACS-ZM001-9 T3, T18 bar;barnase Maize MS6 ACS-ZM005-4 T3, T18 bar; barnase Maize NK603MON-00603-6 T1 cp4 epsps (aroA:CP4) Maize T14 ACS-ZM002-1 T3 pat (syn)Maize T25 ACS-ZM003-2 T3 pat (syn) Maize TC1507 DAS-01507-1 T3, T7cry1Fa2; pat Maize TC6275 DAS-06275-8 T3, T7 mocry1F; bar Maize VIP1034— T3, T7 vip3A; pat Maize 43A47 DP-043A47-3 T3, T7 cry1F; cry34Ab1;cry35Ab1; pat Maize 40416 DP-040416-8 T3, T7 cry1F; cry34Ab1; cry35Ab1;pat Maize 32316 DP-032316-8 T3, T7 cry1F; cry34Ab1; cry35Ab1; pat Maize4114 DP-004114-3 T3, T7 cry1F; cry34Ab1; cry35Ab1; pat Melon Melon A —T22 sam-k Melon Melon B — T22 sam-k Papaya 55-1 CUH-CP551-8 T6 prsv cpPapaya 63-1 CUH-CP631-7 T6 prsv cp Papaya Huanong No. 1 — T6 prsv repPapaya X17-2 UFL-X17CP-6 T6 prsv cp Plum C-5 ARS-PLMC5-6 T6 ppv cpCanola** ZSR500 — T1 cp4 epsps (aroA:CP4); goxv247 Canola** ZSR502 — T1cp4 epsps (aroA:CP4); goxv247 Canola** ZSR503 — T1 cp4 epsps (aroA:CP4);goxv247 Rice 7Crp#242-95-7 — T13 7crp Rice 7Crp#10 — T13 7crp Rice GMShanyou 63 — T7 cry1Ab; cry1Ac Rice Huahui-1/TT51-1 — T7 cry1Ab; cry1AcRice LLRICE06 ACS-OS001-4 T3 bar Rice LLRICE601 BCS-OS003-7 T3 bar RiceLLRICE62 ACS-OS002-5 T3 bar Rice Tarom molaii + cry1Ab — T7 cry1Ab(truncated) Rice GAT-OS2 — T3 bar Rice GAT-OS3 — T3 bar Rice PE-7 — T7Cry1Ac Rice 7Crp#10 — T13 7crp Rice KPD627-8 — T27 OASA1D Rice KPD722-4— T27 OASA1D Rice KA317 — T27 OASA1D Rice HW5 — T27 OASA1D Rice HW1 —T27 OASA1D Rice B-4-1-18 — T28 Δ OsBRI1 Rice G-3-3-22 — T29 OSGA2ox1Rice AD77 — T6 DEF Rice AD51 — T6 DEF Rice AD48 — T6 DEF Rice AD41 — T6DEF Rice 13pNasNa800725atAprt1 — T30 HvNAS1; HvNAAT-A; APRT Rice13pAprt1 — T30 APRT Rice gHvNAS1-gHvNAAT-1 — T30 HvNAS1; HvNAAT-A;HvNAAT-B Rice gHvIDS3-1 — T30 HvIDS3 Rice gHvNAAT1 — T30 HvNAAT-A;HvNAAT-B Rice gHvNAS1-1 — T30 HvNAS1 Rice NIA-OS006-4 — T6 WRKY45 RiceNIA-OS005-3 — T6 WRKY45 Rice NIA-OS004-2 — T6 WRKY45 Rice NIA-OS003-1 —T6 WRKY45 Rice NIA-OS002-9 — T6 WRKY45 Rice NIA-OS001-8 — T6 WRKY45 RiceOsCrl1 — T13 Modified Cry j Rice 17053 — T1 cp4 epsps (aroA:CP4) Rice17314 — T1 cp4 epsps (aroA:CP4) Rose WKS82/130-4-1 IFD-52401-4 T9 5AT;bp40 (f3′5′h) Rose WKS92/130-9-1 IFD-52901-9 T9 5AT; bp40 (f3′5′h)Soybean 260-05 (G94-1, G94-19, — T9 gm-fad2-1 (silencing locus) G168)Soybean A2704-12 ACS-GM005-3 T3 pat Soybean A2704-21 ACS-GM004-2 T3 patSoybean A5547-127 ACS-GM006-4 T3 pat Soybean A5547-35 ACS-GM008-6 T3 patSoybean CV127 BPS-CV127-9 T16 csr1-2 Soybean DAS68416-4 DAS68416-4 T3pat Soybean DP305423 DP-305423-1 T11, T31 gm-fad2-1 (silencing locus);gm-hra Soybean DP356043 DP-356043-5 T1, T31 gm-fad2-1 (silencing locus);gat4601 Soybean FG72 MST-FG072-3 T32, T1 2mepsps; hppdPF W336 SoybeanGTS 40-3-2 (40-3-2) MON-04032-6 T1 cp4 epsps (aroA:CP4) Soybean GU262ACS-GM003-1 T3 pat Soybean MON87701 MON-87701-2 T7 cry1Ac SoybeanMON87705 MON-87705-6 T1, T31 fatb1-A (sense & antisense); fad2- 1A(sense & antisense); cp4 epsps (aroA:CP4) Soybean MON87708 MON-87708-9T1, T12 dmo; cp4 epsps (aroA:CP4) Soybean MON87769 MON-87769-7 T1, T31Pj.D6D; Nc.Fad3; cp4 epsps (aroA:CP4) Soybean MON89788 MON-89788-1 T1cp4 epsps (aroA:CP4) Soybean W62 ACS-GM002-9 T3 bar Soybean W98ACS-GM001-8 T3 bar Soybean MON87754 MON-87754-1 T33 dgat2A SoybeanDAS21606 DAS-21606 T34, T3 Modified aad-12; pat Soybean DAS44406DAS-44406-6 T1, T3, T34 Modified aad-12; 2mepsps; pat Soybean SYHT04RSYN-0004R-8 T35 Modified avhppd Soybean 9582.814.19.1 — T3, T7 cry1Ac,cry1F, PAT Squash CZW3 SEM-ØCZW3-2 T6 cmv cp, zymv cp, wmv cp SquashZW20 SEM-0ZW20-7 T6 zymv cp, wmv cp Sugar Beet GTSB77 (T9100152)SY-GTSB77-8 T1 cp4 epsps (aroA:CP4); goxv247 Sugar Beet H7-1 KM-000H71-4T1 cp4 epsps (aroA:CP4) Sugar Beet T120-7 ACS-BV001-3 T3 pat Sugar BeetT227-1 — T1 cp4 epsps (aroA:CP4) Sugarcane NXI-1T — T21 EcbetA SunflowerX81359 — T16 als Pepper PK-SP01 — T6 cmv cp Tobacco C/F/93/08-02 — T5bxn Tobacco Vector 21-41 — T36 NtQPT1 (antisense) Sunflower X81359 — T16als Wheat MON71800 MON-718ØØ-3 T1 cp4 epsps (aroA:CP4) *Argentine(Brassica napus), **Polish (B. rapa), # Eggplant

Although most typically, compounds of the invention are used to controlundesired vegetation, contact of desired vegetation in the treated locuswith compounds of the invention may result in super-additive orsynergistic effects with genetic traits in the desired vegetation,including traits incorporated through genetic modification. For example,resistance to phytophagous insect pests or plant diseases, tolerance tobiotic/abiotic stresses or storage stability may be greater thanexpected from the genetic traits in the desired vegetation.

Compounds of this invention can also be mixed with one or more otherbiologically active compounds or agents including herbicides, herbicidesafeners, fungicides, insecticides, nematocides, bactericides,acaricides, growth regulators such as insect molting inhibitors androoting stimulants, chemosterilants, semiochemicals, repellents,attractants, pheromones, feeding stimulants, plant nutrients, otherbiologically active compounds or entomopathogenic bacteria, virus orfungi to form a multi-component pesticide giving an even broaderspectrum of agricultural protection. Mixtures of the compounds of theinvention with other herbicides can broaden the spectrum of activityagainst additional weed species, and suppress the proliferation of anyresistant biotypes. Thus the present invention also pertains to acomposition comprising a compound of Formula 1 (in a herbicidallyeffective amount) and at least one additional biologically activecompound or agent (in a biologically effective amount) and can furthercomprise at least one of a surfactant, a solid diluent or a liquiddiluent. The other biologically active compounds or agents can beformulated in compositions comprising at least one of a surfactant,solid or liquid diluent. For mixtures of the present invention, one ormore other biologically active compounds or agents can be formulatedtogether with a compound of Formula 1, to form a premix, or one or moreother biologically active compounds or agents can be formulatedseparately from the compound of Formula 1, and the formulations combinedtogether before application (e.g., in a spray tank) or, alternatively,applied in succession.

A mixture of one or more of the following herbicides with a compound ofthis invention may be particularly useful for weed control: acetochlor,acifluorfen and its sodium salt, aclonifen, acrolein (2-propenal),alachlor, alloxydim, ametryn, amicarbazone, amidosulfuron,aminocyclopyrachlor and its esters (e.g., methyl, ethyl) and salts(e.g., sodium, potassium), aminopyralid, amitrole, ammonium sulfamate,anilofos, asulam, atrazine, azimsulfuron, beflubutamid, benazolin,benazolin-ethyl, bencarbazone, benfluralin, benfuresate,bensulfuron-methyl, bensulide, bentazone, benzobicyclon, benzofenap,bicyclopyrone, bifenox, bilanafos, bispyribac and its sodium salt,bromacil, bromobutide, bromofenoxim, bromoxynil, bromoxynil octanoate,butachlor, butafenacil, butamifos, butralin, butroxydim, butylate,cafenstrole, carbetamide, carfentrazone-ethyl, catechin, chlomethoxyfen,chloramben, chlorbromuron, chlorflurenol-methyl, chloridazon,chlorimuron-ethyl, chlorotoluron, chlorpropham, chlorsulfuron,chlorthal-dimethyl, chlorthiamid, cinidon-ethyl, cinmethylin,cinosulfuron, clacyfos, clefoxydim, clethodim, clodinafop-propargyl,clomazone, clomeprop, clopyralid, clopyralid-olamine,cloransulam-methyl, cumyluron, cyanazine, cycloate, cyclopyrimorate,cyclosulfamuron, cycloxydim, cyhalofop-butyl, 2,4-D and its butotyl,butyl, isoctyl and isopropyl esters and its dimethylammonium, diolamineand trolamine salts, daimuron, dalapon, dalapon-sodium, dazomet, 2,4-DBand its dimethylammonium, potassium and sodium salts, desmedipham,desmetryn, dicamba and its diglycolammonium, dimethylammonium, potassiumand sodium salts, dichlobenil, dichlorprop, diclofop-methyl, diclosulam,difenzoquat metilsulfate, diflufenican, diflufenzopyr, dimefuron,dimepiperate, dimethachlor, dimethametryn, dimethenamid, dimethenamid-P,dimethipin, dimethylarsinic acid and its sodium salt, dinitramine,dinoterb, diphenamid, diquat dibromide, dithiopyr, diuron, DNOC,endothal, EPTC, esprocarb, ethalfluralin, ethametsulfuron-methyl,ethiozin, ethofumesate, ethoxyfen, ethoxysulfuron, etobenzanid,fenoxaprop-ethyl, fenoxaprop-P-ethyl, fenoxasulfone, fenquinotrione,fentrazamide, fenuron, fenuron-TCA, flamprop-methyl,flamprop-M-isopropyl, flamprop-M-methyl, flazasulfuron, florasulam,fluazifop-butyl, fluazifop-P-butyl, fluazolate, flucarbazone,flucetosulfuron, fluchloralin, flufenacet, flufenpyr, flufenpyr-ethyl,flumetsulam, flumiclorac-pentyl, flumioxazin, fluometuron,fluoroglycofen-ethyl, flupoxam, flupyrsulfuron-methyl and its sodiumsalt, flurenol, flurenol-butyl, fluridone, flurochloridone, fluroxypyr,flurtamone, fluthiacet-methyl, fomesafen, foramsulfuron,fosamine-ammonium, glufosinate, glufosinate-ammonium, glufosinate-P,glyphosate and its salts such as ammonium, isopropylammonium, potassium,sodium (including sesquisodium) and trimesium (alternatively namedsulfosate), halauxifen, halauxifen-methyl, halosulfuron-methyl,haloxyfop-etotyl, haloxyfop-methyl, hexazinone, hydantocidin,imazamethabenz-methyl, imazamox, imazapic, imazapyr, imazaquin,imazaquin-ammonium, imazethapyr, imazethapyr-ammonium, imazosulfuron,indanofan, indaziflam, iofensulfuron, iodosulfuron-methyl, ioxynil,ioxynil octanoate, ioxynil-sodium, ipfencarbazone, isoproturon, isouron,isoxaben, isoxaflutole, isoxachlortole, lactofen, lenacil, linuron,maleic hydrazide, MCPA and its salts (e.g., MCPA-dimethylammonium,MCPA-potassium and MCPA-sodium, esters (e.g., MCPA-2-ethylhexyl,MCPA-butotyl) and thioesters (e.g., MCPA-thioethyl), MCPB and its salts(e.g., MCPB-sodium) and esters (e.g., MCPB-ethyl), mecoprop, mecoprop-P,mefenacet, mefluidide, mesosulfuron-methyl, mesotrione, metam-sodium,metamifop, metamitron, metazachlor, metazosulfuron, methabenzthiazuron,methylarsonic acid and its calcium, monoammonium, monosodium anddisodium salts, methyldymron, metobenzuron, metobromuron, metolachlor,S-metolachlor, metosulam, metoxuron, metribuzin, metsulfuron-methyl,molinate, monolinuron, naproanilide, napropamide, napropamide-M,naptalam, neburon, nicosulfuron, norflurazon, orbencarb,orthosulfamuron, oryzalin, oxadiargyl, oxadiazon, oxasulfuron,oxaziclomefone, oxyfluorfen, paraquat dichloride, pebulate, pelargonicacid, pendimethalin, penoxsulam, pentanochlor, pentoxazone, perfluidone,pethoxamid, pethoxyamid, phenmedipham, picloram, picloram-potassium,picolinafen, pinoxaden, piperophos, pretilachlor, primisulfuron-methyl,prodiamine, profoxydim, prometon, prometryn, propachlor, propanil,propaquizafop, propazine, propham, propisochlor, propoxycarbazone,propyrisulfuron, propyzamide, prosulfocarb, prosulfuron, pyraclonil,pyraflufen-ethyl, pyrasulfotole, pyrazogyl, pyrazolynate, pyrazoxyfen,pyrazosulfuron-ethyl, pyribenzoxim, pyributicarb, pyridate, pyriftalid,pyriminobac-methyl, pyrimisulfan, pyrithiobac, pyrithiobac-sodium,pyroxasulfone, pyroxsulam, quinclorac, quinmerac, quinoclamine,quizalofop-ethyl, quizalofop-P-ethyl, quizalofop-P-tefuryl, rimsulfuron,saflufenacil, sethoxydim, siduron, simazine, simetryn, sulcotrione,sulfentrazone, sulfometuron-methyl, sulfosulfuron, 2,3,6-TBA, TCA,TCA-sodium, tebutam, tebuthiuron, tefuryltrione, tembotrione,tepraloxydim, terbacil, terbumeton, terbuthylazine, terbutryn,thenylchlor, thiazopyr, thiencarbazone, thifensulfuron-methyl,thiobencarb, tiafenacil, tiocarbazil, tolpyralate, topramezone,tralkoxydim, tri-allate, triafamone, triasulfuron, triaziflam,tribenuron-methyl, triclopyr, triclopyr-butotyl,triclopyr-triethylammonium, tridiphane, trietazine, trifloxysulfuron,trifludimoxazin, trifluralin, triflusulfuron-methyl, tritosulfuron,vernolate,3-(2-chloro-3,6-difluorophenyl)-4-hydroxy-1-methyl-1,5-naphthyridin-2(1H)-one,5-chloro-3-[(2-hydroxy-6-oxo-1-cyclohexen-1-yl)carbonyl]-1-(4-methoxyphenyl)-2(1H)-quinoxalinone,2-chloro-N-(1-methyl-1H-tetrazol-5-yl)-6-(trifluoromethyl)-3-pyridinecarboxamide,7-(3,5-dichloro-4-pyridinyl)-5-(2,2-difluoroethyl)-8-hydroxypyrido[2,3-b]pyrazin-6(5H)-one),4-(2,6-diethyl-4-methylphenyl)-5-hydroxy-2,6-dimethyl-3(2H)-pyridazinone),5-[[(2,6-difluorophenyl)methoxy]methyl]-4,5-dihydro-5-methyl-3-(3-methyl-2-thienyl)isoxazole(previously methioxolin),4-(4-fluorophenyl)-6-[(2-hydroxy-6-oxo-1-cyclohexen-1-yl)carbonyl]-2-methyl-1,2,4-triazine-3,5(2H,4H)-dione,methyl4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-5-fluoro-2-pyridinecarboxylate,2-methyl-3-(methylsulfonyl)-N-(1-methyl-1H-tetrazol-5-yl)-4-(trifluoromethyl)benzamideand2-methyl-N-(4-methyl-1,2,5-oxadiazol-3-yl)-3-(methylsulfinyl)-4-(trifluoromethyl)benzamide.Other herbicides also include bioherbicides such as Alternaria destruensSimmons, Colletotrichum gloeosporiodes (Penz.) Penz. & Sacc., Drechsieramonoceras (MTB-951), Myrothecium verrucaria (Albertini & Schweinitz)Ditmar: Fries, Phytophthora palmivora (Butl.) Butl. and Pucciniathlaspeos Schub.

Compounds of this invention can also be used in combination with plantgrowth regulators such as aviglycine, N-(phenylmethyl)-1H-purin-6-amine,epocholeone, gibberellic acid, gibberellin A₄ and A₇, harpin protein,mepiquat chloride, prohexadione calcium, prohydrojasmon, sodiumnitrophenolate and trinexapac-methyl, and plant growth modifyingorganisms such as Bacillus cereus strain BP01.

General references for agricultural protectants (i.e. herbicides,herbicide safeners, insecticides, fungicides, nematocides, acaricidesand biological agents) include The Pesticide Manual, 13th Edition, C. D.S. Tomlin, Ed., British Crop Protection Council, Famham, Surrey, U.K.,2003 and The BioPesticide Manual, 2nd Edition, L. G. Copping, Ed.,British Crop Protection Council, Farnham, Surrey, U.K., 2001.

For embodiments where one or more of these various mixing partners areused, the mixing partners are typically used in the amounts similar toamounts customary when the mixture partners are used alone. Moreparticularly in mixtures, active ingredients are often applied at anapplication rate between one-half and the full application ratespecified on product labels for use of active ingredient alone. Theseamounts are listed in references such as The Pesticide Manual and TheBioPesticide Manual. The weight ratio of these various mixing partners(in total) to the compound of Formula 1 is typically between about1:3000 and about 3000:1. Of note are weight ratios between about 1:300and about 300:1 (for example ratios between about 1:30 and about 30:1).One skilled in the art can easily determine through simpleexperimentation the biologically effective amounts of active ingredientsnecessary for the desired spectrum of biological activity. It will beevident that including these additional components may expand thespectrum of weeds controlled beyond the spectrum controlled by thecompound of Formula 1 alone.

In certain instances, combinations of a compound of this invention withother biologically active (particularly herbicidal) compounds or agents(i.e. active ingredients) can result in a greater-than-additive (i.e.synergistic) effect on weeds and/or a less-than-additive effect (i.e.safening) on crops or other desirable plants. Reducing the quantity ofactive ingredients released in the environment while ensuring effectivepest control is always desirable. Ability to use greater amounts ofactive ingredients to provide more effective weed control withoutexcessive crop injury is also desirable. When synergism of herbicidalactive ingredients occurs on weeds at application rates givingagronomically satisfactory levels of weed control, such combinations canbe advantageous for reducing crop production cost and decreasingenvironmental load. When safening of herbicidal active ingredientsoccurs on crops, such combinations can be advantageous for increasingcrop protection by reducing weed competition.

Of note is a combination of a compound of the invention with at leastone other herbicidal active ingredient. Of particular note is such acombination where the other herbicidal active ingredient has differentsite of action from the compound of the invention. In certain instances,a combination with at least one other herbicidal active ingredienthaving a similar spectrum of control but a different site of action willbe particularly advantageous for resistance management. Thus, acomposition of the present invention can further comprise (in aherbicidally effective amount) at least one additional herbicidal activeingredient having a similar spectrum of control but a different site ofaction.

Compounds of this invention can also be used in combination withherbicide safeners such as allidochlor, benoxacor, cloquintocet-mexyl,cumyluron, cyometrinil, cyprosulfonamide, daimuron, dichlormid,dicyclonon, dietholate, dimepiperate, fenchlorazole-ethyl, fenclorim,flurazole, fluxofenim, furilazole, isoxadifen-ethyl, mefenpyr-diethyl,mephenate, methoxyphenone naphthalic anhydride (1,8-naphthalicanhydride), oxabetrinil, N-(aminocarbonyl)-2-methylbenzenesulfonamide,N-(aminocarbonyl)-2-fluorobenzenesulfonamide,1-bromo-4-[(chloromethyl)sulfonyl]benzene (BCS),4-(dichloroacetyl)-1-oxa-4-azospiro[4.5]decane (MON 4660),2-(dichloromethyl)-2-methyl-1,3-dioxolane (MG 191), ethyl1,6-dihydro-1-(2-methoxyphenyl)-6-oxo-2-phenyl-5-pyrimidinecarboxylate,2-hydroxy-N,N-dimethyl-6-(trifluoromethyl)pyridine-3-carboxamide, and3-oxo-1-cyclohexen-1-yl1-(3,4-dimethylphenyl)-1,6-dihydro-6-oxo-2-phenyl-5-pyrimidinecarboxylate,2,2-dichloro-1-(2,5-trimethyl-3-oxazolidinyl)-ethanone and2-methoxy-N-[[4-[[(methylamino)carbonyl]amino]phenyl]sulfonyl]-benzamideto increase safety to certain crops. Antidotally effective amounts ofthe herbicide safeners can be applied at the same time as the compoundsof this invention, or applied as seed treatments. Therefore an aspect ofthe present invention relates to a herbicidal mixture comprising acompound of this invention and an antidotally effective amount of aherbicide safener. Seed treatment is particularly useful for selectiveweed control, because it physically restricts antidoting to the cropplants. Therefore a particularly useful embodiment of the presentinvention is a method for selectively controlling the growth ofundesired vegetation in a crop comprising contacting the locus of thecrop with a herbicidally effective amount of a compound of thisinvention wherein seed from which the crop is grown is treated with anantidotally effective amount of safener. Antidotally effective amountsof safeners can be easily determined by one skilled in the art throughsimple experimentation.

Compounds of the invention cans also be mixed with: (1) polynucleotidesincluding but not limited to DNA, RNA, and/or chemically modifiednucleotides influencing the amount of a particular target through downregulation, interference, suppression or silencing of the geneticallyderived transcript that render a herbicidal effect; or (2)polynucleotides including but not limited to DNA, RNA, and/or chemicallymodified nucleotides influencing the amount of a particular targetthrough down regulation, interference, suppression or silencing of thegenetically derived transcript that render a safening effect.

Of note is a composition comprising a compound of the invention (in aherbicidally effective amount), at least one additional activeingredient selected from the group consisting of other herbicides andherbicide safeners (in an effective amount), and at least one componentselected from the group consisting of surfactants, solid diluents andliquid diluents.

Table A1 lists specific combinations of a Component (a) with Component(b) illustrative of the mixtures, compositions and methods of thepresent invention. Compound 1 in the Component (a) column is identifiedin Index Tables A. The second column of Table A1 lists the specificComponent (b) compound (e.g., “2,4-D” in the first line). The third,fourth and fifth columns of Table A1 lists ranges of weight ratios forrates at which the Component (a) compound is typically applied to afield-grown crop relative to Component (b) (i.e. (a):(b)). Thus, forexample, the first line of Table A1 specifically discloses thecombination of Component (a) (i.e. Compound 1 in Index Table A) with2,4-D is typically applied in a weight ratio between 1:192-6:1. Theremaining lines of Table A1 are to be construed similarly.

TABLE A1 Component (a) Typical More Typical Most Typical (Compound #)Component (b) Weight Ratio Weight Ratio Weight Ratio 1 2,4-D 1:192-6:11:64-2:1 1:24-1:3 1 Acetochlor 1:768-2:1 1:256-1:2   1:96-1:11 1Acifluorfen  1:96-12:1 1:32-4:1 1:12-1:2 1 Aclonifen 1:857-2:11:285-1:3  1:107-1:12 1 Alachlor 1:768-2:1 1:256-1:2   1:96-1:11 1Ametryn 1:384-3:1 1:128-1:1  1:48-1:6 1 Amicarbazone 1:192-6:1 1:64-2:11:24-1:3 1 Amidosulfuron   1:6-168:1  1:2-56:1  1:1-11:1 1Aminocyclopyrachlor  1:48-24:1 1:16-8:1  1:6-2:1 1 Aminopyralid 1:20-56:1  1:6-19:1  1:2-4:1 1 Amitrole 1:768-2:1 1:256-1:2   1:96-1:111 Anilofos  1:96-12:1 1:32-4:1 1:12-1:2 1 Asulam 1:960-2:1 1:320-1:3 1:120-1:14 1 Atrazine 1:192-6:1 1:64-2:1 1:24-1:3 1 Azimsulfuron  1:6-168:1  1:2-56:1  1:1-11:1 1 Beflubutamid 1:342-4:1 1:114-2:1 1:42-1:5 1 Benfuresate 1:617-2:1 1:205-1:2  1:77-1:9 1Bensulfuron-methyl  1:25-45:1  1:8-15:1  1:3-3:1 1 Bentazone 1:192-6:11:64-2:1 1:24-1:3 1 Benzobicyclon  1:85-14:1 1:28-5:1 1:10-1:2 1Benzofenap 1:257-5:1 1:85-2:1 1:32-1:4 1 Bicyclopyrone  1:42-27:11:14-9:1  1:5-2:1 1 Bifenox 1:257-5:1 1:85-2:1 1:32-1:4 1Bispyribac-sodium   1:10-112:1  1:3-38:1  1:1-7:1 1 Bromacil 1:384-3:11:128-1:1  1:48-1:6 1 Bromobutide 1:384-3:1 1:128-1:1  1:48-1:6 1Bromoxynil  1:96-12:1 1:32-4:1 1:12-1:2 1 Butachlor 1:768-2:1 1:256-1:2  1:96-1:11 1 Butafenacil  1:42-27:1 1:14-9:1  1:5-2:1 1 Butylate1:1542-1:2  1:514-1:5  1:192-1:22 1 Carfenstrole 1:192-6:1 1:64-2:11:24-1:3 1 Carfentrazone-ethyl 1:128-9:1 1:42-3:1 1:16-1:2 1Chlorimuron-ethyl   1:8-135:1  1:2-45:1  1:1-9:1 1 Chlorotoluron1:768-2:1 1:256-1:2   1:96-1:11 1 Chlorsulfuron   1:6-168:1  1:2-56:1 1:1-11:1 1 Cincosulfuron  1:17-68:1  1:5-23:1  1:2-5:1 1 Cinidon-ethyl1:384-3:1 1:128-1:1  1:48-1:6 1 Cinmethylin  1:34-34:1  1:11-12:1 1:4-3:1 1 Clacyfos  1:34-34:1  1:11-12:1  1:4-3:1 1 Clethodim 1:48-24:1 1:16-8:1  1:6-2:1 1 Clodinafop-propargyl  1:20-56:1  1:6-19:1 1:2-4:1 1 Clomazone 1:384-3:1 1:128-1:1  1:48-1:6 1 Clomeprop 1:171-7:11:57-3:1 1:21-1:3 1 Clopyralid 1:192-6:1 1:64-2:1 1:24-1:3 1Cloransulam-methyl  1:12-96:1  1:4-32:1  1:1-6:1 1 Cumyluron 1:384-3:11:128-1:1  1:48-1:6 1 Cyanazine 1:384-3:1 1:128-1:1  1:48-1:6 1Cyclopyrimorate  1:17-68:1  1:5-23:1  1:2-5:1 1 Cyclosulfamuron 1:17-68:1  1:5-23:1  1:2-5:1 1 Cycloxydim  1:96-12:1 1:32-4:1 1:12-1:21 Cyhalofop  1:25-45:1  1:8-15:1  1:3-3:1 1 Daimuron 1:192-6:1 1:64-2:11:24-1:3 1 Desmedipham 1:322-4:1 1:107-2:1  1:40-1:5 1 Dicamba 1:192-6:11:64-2:1 1:24-1:3 1 Dichlobenil 1:1371-1:2  1:457-1:4  1:171-1:20 1Dichlorprop 1:925-2:1 1:308-1:3  1:115-1:13 1 Diclofop-methyl 1:384-3:11:128-1:1  1:48-1:6 1 Diclosulam   1:10-112:1  1:3-38:1  1:1-7:1 1Difenzoquat 1:288-4:1 1:96-2:1 1:36-1:4 1 Diflufenican 1:857-2:11:285-1:3  1:107-1:12 1 Diflufenzopyr  1:12-96:1  1:4-32:1  1:1-6:1 1Dimethachlor 1:768-2:1 1:256-1:2   1:96-1:11 1 Dimethametryn 1:192-6:11:64-2:1 1:24-1:3 1 Dimethenamid-P 1:384-3:1 1:128-1:1  1:48-1:6 1Dithiopyr 1:192-6:1 1:64-2:1 1:24-1:3 1 Diuron 1:384-3:1 1:128-1:1 1:48-1:6 1 EPTC 1:768-2:1 1:256-1:2   1:96-1:11 1 Esprocarb 1:1371-1:2 1:457-1:4  1:171-1:20 1 Ethalfluralin 1:384-3:1 1:128-1:1  1:48-1:6 1Ethametsulfuron-methyl  1:17-68:1  1:5-23:1  1:2-5:1 1 Ethoxyfen  1:8-135:1  1:2-45:1  1:1-9:1 1 Ethoxysulfuron  1:20-56:1  1:6-19:1 1:2-4:1 1 Etobenzanid 1:257-5:1 1:85-2:1 1:32-1:4 1 Fenoxaprop-ethyl 1:120-10:1 1:40-4:1 1:15-1:2 1 Fenoxasulfone  1:85-14:1 1:28-5:11:10-1:2 1 Fenquinotrione  1:17-68:1  1:5-23:1  1:2-5:1 1 Fentrazamide 1:17-68:1  1:5-23:1  1:2-5:1 1 Flazasulfuron  1:17-68:1  1:5-23:1 1:2-5:1 1 Florasulam   1:2-420:1   1:1-140:1  2:1-27:1 1Fluazifop-butyl 1:192-6:1 1:64-2:1 1:24-1:3 1 Flucarbazone   1:8-135:1 1:2-45:1  1:1-9:1 1 Flucetosulfuron   1:8-135:1  1:2-45:1  1:1-9:1 1Flufenacet 1:257-5:1 1:85-2:1 1:32-1:4 1 Flumetsulam  1:24-48:1 1:8-16:1  1:3-3:1 1 Flumiclorac-pentyl   1:10-112:1  1:3-38:1  1:1-7:11 Flumioxazin  1:25-45:1  1:8-15:1  1:3-3:1 1 Fluometuron 1:384-3:11:128-1:1  1:48-1:6 1 Flupyrsulfuron-methyl   1:3-336:1   1:1-112:1 2:1-21:1 1 Fluridone 1:384-3:1 1:128-1:1  1:48-1:6 1 Fluroxypyr 1:96-12:1 1:32-4:1 1:12-1:2 1 Flurtamone 1:857-2:1 1:285-1:3 1:107-1:12 1 Fluthiacet-methyl  1:48-42:1  1:16-14:1  1:3-3:1 1Fomesafen  1:96-12:1 1:32-4:1 1:12-1:2 1 Foramsulfuron  1:13-84:1 1:4-28:1  1:1-6:1 1 Glufosinate 1:288-4:1 1:96-2:1 1:36-1:4 1Glyphosate 1:288-4:1 1:96-2:1 1:36-1:4 1 Halosulfuron-methyl  1:17-68:1 1:5-23:1  1:2-5:1 1 Halauxifen  1:20-56:1  1:6-19:1  1:2-4:1 1Halauxifen methyl  1:20-56:1  1:6-19:1  1:2-4:1 1 Haloxyfop-methyl 1:34-34:1  1:11-12:1  1:4-3:1 1 Hexazinone 1:192-6:1 1:64-2:1 1:24-1:31 Hydantocidin 1:1100-16:1 1:385-8:1  1:144-4:1  1 Imazamox  1:13-84:1 1:4-28:1  1:1-6:1 1 Imazapic  1:20-56:1  1:6-19:1  1:2-4:1 1 Imazapyr 1:85-14:1 1:28-5:1 1:10-1:2 1 Imazaquin  1:34-34:1  1:11-12:1  1:4-3:11 Imazethabenz-methyl 1:171-7:1 1:57-3:1 1:21-1:3 1 Imazethapyr 1:24-48:1  1:8-16:1  1:3-3:1 1 Imazosulfuron  1:27-42:1  1:9-14:1 1:3-3:1 1 Indanofan 1:342-4:1 1:114-2:1  1:42-1:5 1 Indaziflam 1:25-45:1  1:8-15:1  1:3-3:1 1 Iodosulfuron-methyl   1:3-336:1  1:1-112:1  2:1-21:1 1 Ioxynil 1:192-6:1 1:64-2:1 1:24-1:3 1Ipfencarbazone  1:85-14:1 1:28-5:1 1:10-1:2 1 Isoproturon 1:384-3:11:128-1:1  1:48-1:6 1 Isoxaben 1:288-4:1 1:96-2:1 1:36-1:4 1Isoxaflutole  1:60-20:1 1:20-7:1  1:7-2:1 1 Lactofen  1:42-27:1 1:14-9:1 1:5-2:1 1 Lenacil 1:384-3:1 1:128-1:1  1:48-1:6 1 Linuron 1:384-3:11:128-1:1  1:48-1:6 1 MCPA 1:192-6:1 1:64-2:1 1:24-1:3 1 MCPB 1:288-4:11:96-2:1 1:36-1:4 1 Mecoprop 1:768-2:1 1:256-1:2   1:96-1:11 1 Mefenacet1:384-3:1 1:128-1:1  1:48-1:6 1 Mefluidide 1:192-6:1 1:64-2:1 1:24-1:3 1Mesosulfuron-methyl   1:5-224:1  1:1-75:1  1:1-14:1 1 Mesotrione 1:42-27:1 1:14-9:1  1:5-2:1 1 Metamifop  1:42-27:1 1:14-9:1  1:5-2:1 1Metazachlor 1:384-3:1 1:128-1:1  1:48-1:6 1 Metazosulfuron  1:25-45:1 1:8-15:1  1:3-3:1 1 Methabenzthiazuron 1:768-2:1 1:256-1:2   1:96-1:111 Metolachlor 1:768-2:1 1:256-1:2   1:96-1:11 1 Metosulam   1:8-135:1 1:2-45:1  1:1-9:1 1 Metribuzin 1:192-6:1 1:64-2:1 1:24-1:3 1Metsulfuron-methyl   1:2-560:1   1:1-187:1  3:1-35:1 1 Molinate1:1028-2:1  1:342-1:3  1:128-1:15 1 Napropamide 1:384-3:1 1:128-1:1 1:48-1:6 1 Napropamide-M 1:192-6:1 1:64-2:1 1:24-1:3 1 Naptalam1:192-6:1 1:64-2:1 1:24-1:3 1 Nicosulfuron  1:12-96:1  1:4-32:1  1:1-6:11 Norflurazon 1:1152-1:1  1:384-1:3  1:144-1:16 1 Orbencarb 1:1371-1:2 1:457-1:4  1:171-1:20 1 Orthosulfamuron  1:20-56:1  1:6-19:1  1:2-4:1 1Oryzalin 1:514-3:1 1:171-1:2  1:64-1:8 1 Oxadiargyl 1:384-3:1 1:128-1:1 1:48-1:6 1 Oxadiazon 1:548-3:1 1:182-1:2  1:68-1:8 1 Oxasulfuron 1:27-42:1  1:9-14:1  1:3-3:1 1 Oxaziclomefone  1:42-27:1 1:14-9:1 1:5-2:1 1 Oxyfluorfen 1:384-3:1 1:128-1:1  1:48-1:6 1 Paraquat1:192-6:1 1:64-2:1 1:24-1:3 1 Pendimethalin 1:384-3:1 1:128-1:1 1:48-1:6 1 Penoxsulam   1:10-112:1  1:3-38:1  1:1-7:1 1 Penthoxamid1:384-3:1 1:128-1:1  1:48-1:6 1 Pentoxazone  1:102-12:1 1:34-4:11:12-1:2 1 Phenmedipham  1:102-12:1 1:34-4:1 1:12-1:2 1 Picloram 1:96-12:1 1:32-4:1 1:12-1:2 1 Picolinafen  1:34-34:1  1:11-12:1 1:4-3:1 1 Pinoxaden  1:25-45:1  1:8-15:1  1:3-3:1 1 Pretilachlor1:192-6:1 1:64-2:1 1:24-1:3 1 Primisulfuron-methyl   1:8-135:1  1:2-45:1 1:1-9:1 1 Prodiamine 1:384-3:1 1:128-1:1  1:48-1:6 1 Profoxydim 1:42-27:1 1:14-9:1  1:5-2:1 1 Prometryn 1:384-3:1 1:128-1:1  1:48-1:6 1Propachlor 1:1152-1:1  1:384-1:3  1:144-1:16 1 Propanil 1:384-3:11:128-1:1  1:48-1:6 1 Propaquizafop  1:48-24:1 1:16-8:1  1:6-2:1 1Propoxycarbazone  1:17-68:1  1:5-23:1  1:2-5:1 1 Propyrisulfuron 1:17-68:1  1:5-23:1  1:2-5:1 1 Propyzamide 1:384-3:1 1:128-1:1 1:48-1:6 1 Prosulfocarb 1:1200-1:2  1:400-1:4  1:150-1:17 1 Prosulfuron  1:6-168:1  1:2-56:1  1:1-11:1 1 Pyraclonil  1:42-27:1 1:14-9:1 1:5-2:1 1 Pyraflufen-ethyl   1:5-224:1  1:1-75:1  1:1-14:1 1Pyrasulfotole  1:13-84:1  1:4-28:1  1:1-6:1 1 Pyrazolynate 1:857-2:11:285-1:3  1:107-1:12 1 Pyrazosulfuron-ethyl   1:10-112:1  1:3-38:1 1:1-7:1 1 Pyrazoxyfen   1:5-224:1  1:1-75:1  1:1-14:1 1 Pyribenzoxim  1:10-112:1  1:3-38:1  1:1-7:1 1 Pyributicarb 1:384-3:1 1:128-1:1 1:48-1:6 1 Pyridate 1:288-4:1 1:96-2:1 1:36-1:4 1 Pyriftalid  1:10-112:1  1:3-38:1  1:1-7:1 1 Pyriminobac-methyl  1:20-56:1 1:6-19:1  1:2-4:1 1 Pyrimisulfan  1:17-68:1  1:5-23:1  1:2-5:1 1Pyrithiobac  1:24-48:1  1:8-16:1  1:3-3:1 1 Pyroxasulfone  1:85-14:11:28-5:1 1:10-1:2 1 Pyroxsulam   1:5-224:1  1:1-75:1  1:1-14:1 1Quinclorac 1:192-6:1 1:64-2:1 1:24-1:3 1 Quizalofop-ethyl  1:42-27:11:14-9:1  1:5-2:1 1 Rimsulfuron  1:13-84:1  1:4-28:1  1:1-6:1 1Saflufenacil  1:25-45:1  1:8-15:1  1:3-3:1 1 Sethoxydim  1:96-12:11:32-4:1 1:12-1:2 1 Simazine 1:384-3:1 1:128-1:1  1:48-1:6 1 Sulcotrione 1:120-10:1 1:40-4:1 1:15-1:2 1 Sulfentrazone 1:147-8:1 1:49-3:11:18-1:3 1 Sulfometuron-methyl  1:34-34:1  1:11-12:1  1:4-3:1 1Sulfosulfuron   1:8-135:1  1:2-45:1  1:1-9:1 1 Tebuthiuron 1:384-3:11:128-1:1  1:48-1:6 1 Tefuryltrione  1:42-27:1 1:14-9:1  1:5-2:1 1Tembotrione  1:31-37:1  1:10-13:1  1:3-3:1 1 Tepraloxydim  1:25-45:1 1:8-15:1  1:3-3:1 1 Terbacil 1:288-4:1 1:96-2:1 1:36-1:4 1Terbuthylazine 1:857-2:1 1:285-1:3  1:107-1:12 1 Terbutryn 1:192-6:11:64-2:1 1:24-1:3 1 Thenylchlor  1:85-14:1 1:28-5:1 1:10-1:2 1 Thiazopyr1:384-3:1 1:128-1:1  1:48-1:6 1 Thiencarbazone   1:3-336:1   1:1-112:1 2:1-21:1 1 Thifensulfuron-methyl   1:5-224:1  1:1-75:1  1:1-14:1 1Tiafenacil  1:17-68:1  1:5-23:1  1:2-5:1 1 Thiobencarb 1:768-2:11:256-1:2   1:96-1:11 1 Tolpyralate  1:31-37:1  1:10-13:1  1:3-3:1 1Topramzone   1:6-168:1  1:2-56:1  1:1-11:1 1 Tralkoxydim  1:68-17:11:22-6:1  1:8-2:1 1 Triafamone   1:2-420:1   1:1-140:1  2:1-27:1 1Triallate 1:768-2:1 1:256-1:2   1:96-1:11 1 Triasulfuron   1:5-224:1 1:1-75:1  1:1-14:1 1 Triaziflam 1:171-7:1 1:57-3:1 1:21-1:3 1Tribenuron-methyl   1:3-336:1   1:1-112:1  2:1-21:1 1 Triclopyr1:192-6:1 1:64-2:1 1:24-1:3 1 Trifloxysulfuron   1:2-420:1   1:1-140:1 2:1-27:1 1 Trifludimoxazin  1:25-45:1  1:8-15:1  1:3-3:1 1 Trifluralin1:288-4:1 1:96-2:1 1:36-1:4 1 Triflusulfuron-methyl  1:17-68:1  1:5-23:1 1:2-5:1 1 Tritosulfuron  1:13-84:1  1:4-28:1  1:1-6:1

Table A2 is constructed the same as Table A1 above except that entriesbelow the “Component (a)” column heading are replaced with therespective Component (a) Column Entry shown below. Compound 2 in theComponent (a) column is identified in Index Table A. Thus, for example,in Table A2 the entries below the “Component (a)” column heading allrecite “Compound 2” (i.e. Compound 2 identified in Index Table A), andthe first line below the column headings in Table A2 specificallydiscloses a mixture of Compound 2 with 2,4-D. Tables A3 through A4 areconstructed similarly.

Table Number Component (a) Column Entries A2 Compound 2 A3 Compound 5 A4Compound 6 A5 Compound 3 A6 Compound 4 A7 Compound 7 A8 Compound 8 A9Compound 9 A10 Compound 10 A11 Compound 11 A12 Compound 12 A13 Compound13 A14 Compound 14

Preferred for better control of undesired vegetation (e.g., lower userate such as from synergism, broader spectrum of weeds controlled, orenhanced crop safety) or for preventing the development of resistantweeds are mixtures of a compound of this invention with a herbicideselected from the group consisting of chlorimuron-ethyl, nicosulfuron,diuron, hexazinoe, thifensulfuron-methyl and S-metolachlor.

The compounds of the present invention are useful for the control ofweed species that are resistant to herbicides with the AHAS-inhibitor or(b2) [chemical compound that inhibits acetohydroxy acid synthase (AHAS),also known as acetolactate synthase (ALS)] mode of action.

The following Tests demonstrate the control efficacy of the compounds ofthis invention against specific weeds. The weed control afforded by thecompounds is not limited, however, to these species. See Index Tables Aand B for compound descriptions. The following abbreviations are used inthe Index Tables which follow: t is tertiary, s is secondary, n isnormal, i is iso, c is cyclo, Me is methyl, Et is ethyl, Pr is propyl,i-Pr is isopropyl, t-Bu is tertiary-butyl, i-Pr is iso-propyl, c-Pr iscyclopropyl, Ph is phenyl, OMe is methoxy, OEt is ethoxy, SMe ismethylthio, SEt is ethylthio and —CN is cyano. The abbreviation “Cmpd.No.” stands for “Compound Number”. Mass spectra are reported with anestimated precision within +0.5 Da as the molecular weight of thehighest isotopic abundance parent ion (M+1) formed by addition of H⁺(molecular weight of 1) to the molecule observed by using atmosphericpressure chemical ionization (AP+).

INDEX TABLE A

M.S.(AP+) No. Q R² (R³)_(m) or m.p. 1 (Ex. 2) 4-Br-1H-pyrazol-1-yl Cl m= 0   129-131  2 4-Cl-1H-pyrazol-1-yl Cl m = 0   138-140  34-CH₃-1H-pyrazol-1-yl Cl m = 0   110-113  4 4-Ph-1H-pyrazol-1-yl Cl m =0   130-132  5 3-CF₂H-5-isoxazolyl Cl m = 0 325 6 (Ex. 1)5-CF₂H-3-isoxazolyl Cl m = 0   100-104  7 3-CF₂H-5-isoxazolyl F m = 0  100-104 10 4-Br-1H-pyrazol-1-yl Cl 6-CH₃ 367 12 (Ex. 3)(5-Cl-pyridin-2-yl) Cl m = 0 319 13 (3-CF₃-1H-pyrazol-1-yl) Cl 5-CH₃103.5-109 14 (2-CF₃-pyridin-4-yl) Cl m = 0 353

INDEX TABLE B

M.S.(AP+) No. Q R² (R³)_(m) or m.p. 8 (Ex. 1) 5-CF₂H-3-isoxazolyl Cl m =0 139-143  9 4-Cl-1H-pyrazol-1-yl F m = 0 129-133 114-Br-1H-pyrazol-1-yl Cl m = 0 368

Biological Examples of the Invention

Test A

Seeds of plant species selected from bamyardgrass (Echinochloacrus-galli), kochia (Kochia scoparia), ragweed (common ragweed, Ambrosiaelatior), ryegrass, Italian (Italian ryegrass, Lolium multiflorum),foxtail, giant (giant foxtail, Setaria faberii), pigweed (Amaranthusretroflexus), crabgrass, large (large crabgrass, Digitaria sanguinalis),momingglory (Ipomoea spp.), velvetleaf (Abutilon theophrasti), wheat(Triticum aestivum), and corn (Zea mays) were planted into a blend ofloam soil and sand and treated preemergence with a directed soil sprayusing test chemicals formulated in a non-phytotoxic solvent mixturewhich included a surfactant.

At the same time, plants selected from these crop and weed species andalso blackgrass (Alopecurus myosuroides), and galium (catchweedbedstraw, Galium aparine) were planted in pots containing the same blendof loam soil and sand and treated with postemergence applications oftest chemicals formulated in the same manner. Plants ranged in heightfrom 2 to 10 cm and were in the one- to two-leaf stage for thepostemergence treatment. Treated plants and untreated controls weremaintained in a greenhouse for approximately 10 days, after which timeall treated plants were compared to untreated controls and visuallyevaluated for injury. Plant response ratings, summarized in Table A, arebased on a 0 to 100 scale where 0 is no effect and 100 is completecontrol. A dash (-) response means no test result.

TABLE A Compound 1000 g ai/ha 11 Postemergence Barnyardgrass 0Blackgrass 10 Corn 0 Foxtail, Giant 0 Galium 40 Kochia 60 Pigweed 90Ragweed 20 Ryegrass, Italian 0 Wheat 0 Compounds 500 g ai/ha 1 2 3 4 1014 Post- emergence Barnyard 10 20 10 20 0 60 grass Blackgrass — — — — —90 Corn 20 10 10 30 0 40 Crabgrass, 50 40 10 0 10 — Large Foxtail, 30 3010 0 0 90 Giant Galium — — — — — 90 Kochia — — — — — 100 Morning- 80 8030 10 10 — glory Pigweed 100 100 40 70 50 100 Ragweed — — — — — 30Ryegrass, — — — — — 40 Italian Velvetleaf 50 70 20 0 80 — Wheat 20 20 100 0 10 Compounds 125 g ai/ha 1 2 3 4 5 6 7 8 9 10 12 13 14 Post-emergence Barnyard-  0 0 0 0 20 30  0 10 0 0 30 0 40 grass Blackgrass —— — — 20 20  0 10 0 — 0 0 10 Corn 10 0 0 0 10 30  0 20 0 0 10 0 20Crabgrass, 10 10 10 0 — — — — — 0 — — — Large Foxtail, 10 0 0 0 10 40  010 0 0 0 0 60 Giant Galium — — — — 60 70 50 60 30 — 10 0 50 Kochia — — —— 90 100 90 70 50 — 40 0 80 Morning- 10 40 20 0 — — — — — 0 — — — gloryPigweed 90 100 10 20 90 100 70 70 50 10 30 0 100 Ragweed — — — — 60 4010 50 30 — 10 0 10 Ryegrass, — — — — 0 10  0 0 0 — 0 0 30 ItalianVelvetleaf 20 20 10 0 — — — — — 50 — — — Wheat 10 10 10 0 10 30 20 20 00 0 0 0 Compounds 31 g ai/ha 5 6 7 8 9 12 13 Post- emergence Barnyard- 010 0 0 0 0 0 grass Blackgrass 0 0 0 0 0 0 0 Corn 0 20 0 0 0 0 0 Foxtail,0 20 0 0 0 0 0 Giant Galium 40 50 20 40 10 10 0 Kochia 80 90 70 40 10 00 Pigweed 80 70 20 50 30 10 0 Ragweed 20 20 0 30 10 0 0 Ryegrass, 0 0 00 0 0 0 Italian Wheat 0 20 0 10 0 0 0 1000 Compound g ai/ha 11Preemergence Barnyardgrass 0 Foxtail, Giant 0 Kochia 30 Pigweed 100Ragweed 30 Ryegrass, Italian 0 500 g Compounds ai/ha 1 2 3 4 10 14 Pre-emergence Barnyard- 50 40 0 0 0 100 grass Corn 0 0 0 0 0 — Crabgrass,100 100 0 0 50 — Large Foxtail, 80 80 0 0 20 100 Giant Kochia — — — — —100 Morning- 0 0 0 0 10 — glory Pigweed 90 90 10 0 40 100 Ragweed — — —— — 20 Ryegrass, — — — — — 20 Italian Velvetleaf 30 30 0 0 20 — Wheat 1010 0 0 0 — Compounds 125 g ai/ha 1 2 3 4 5 6 7 8 9 10 12 13 14 Pre-emergence Barnyard- 10 0 0 0 20 70 20 0 0 0 0 0 40 grass Corn 0 0 0 0 —— — — — 0 — — — Crabgrass, 40 — 0 0 — — — — — 0 — — — Large Foxtail, 2010 0 0 80 90 20 10 0 0 0 0 90 Giant Kochia — — — — 80 90 70 40 0 — 40 0100 Morning- — 0 0 0 — — — — — 0 — — — glory Pigweed 50 70 0 0 100 100100 90 20 0 60 0 100 Ragweed — — — — 10 50 30 0 0 — 0 0 0 Ryegrass, — —— — 0 0 0 0 0 — 0 0 10 Italian Velvetleaf 10 10 0 0 — — — — — 0 — — —Wheat 0 0 0 0 — — — — — 0 — — — Compounds 31 g ai/ha 5 6 7 8 9 12 13Pre- emergence Barnyard- 0 0 0 0 0 0 0 grass Foxtail, 10 0 0 0 0 0 0Giant Kochia 10 60 20 0 0 0 0 Pigweed 80 90 70 40 0 0 0 Ragweed 0 0 0 00 0 0 Ryegrass, 0 0 0 0 0 0 0 ItalianTest B

Plant species in the flooded paddy test selected from rice (Oryzasativa), sedge, umbrella (small-flower umbrella sedge, Cyperusdifformis), ducksalad (Heteranthera limosa), and barnyardgrass(Echinochloa crus-galli) were grown to the 2-leaf stage for testing. Attime of treatment, test pots were flooded to 3 cm above the soilsurface, treated by application of test compounds directly to the paddywater, and then maintained at that water depth for the duration of thetest. Treated plants and controls were maintained in a greenhouse for 13to 15 days, after which time all species were compared to controls andvisually evaluated. Plant response ratings, summarized in Table B, arebased on a scale of 0 to 100 where 0 is no effect and 100 is completecontrol. A dash (-) response means no test result.

TABLE B 250 g Compounds ai/ha 1 2 3 4 5 6 7 8 9 10 12 13 14 FloodBarnyard- 0 0 0 — 0 0 0 0 0 0 0 0 0 grass Ducksalad 60 80 0 0 75 30 5040 0 0 30 0 40 Rice 0 0 0 10 0 0 0 0 0 0 20 0 0 Sedge, 50 75 60 70 80 00 0 0 0 30 0 50 UmbrellaTest C

Seeds of plant species selected from blackgrass (Alopecurusmyosuroides), ryegrass, Italian (Italian ryegrass, Lolium multiflorum),wheat (winter wheat, Triticum aestivum), galium (catchweed bedstraw,Galium aparine), corn (Zea mays), crabgrass, large (large crabgrass,Digitaria sanguinalis), foxtail, giant (giant foxtail, Setaria faberii),lambsquarters (Chenopodium album), morningglory (Ipomoea coccinea),nutsedge, yellow (yellow nutsedge, Cyperus esculentus), pigweed(Amaranthus retroflexus), johnsongrass (Sorghum halepense), ragweed(common ragweed, Ambrosia elatior), soybean (Glycine max), barnyardgrass(Echinochloa crus-galli), oilseed rape (Brassica napus), waterhemp(common waterhemp, Amaranthus rudis), chickweed (common chickweed,Stellaria media), oat, wild (wild oat, Avena fatua), kochia (Kochiascoparia), and velvetleaf (Abutilon theophrasti) were planted in potscontaining Redi-Earth® planting medium (Scotts Company, 14111 ScottslawnRoad, Marysville, Ohio 43041) comprising spaghnum peat moss,vermiculite, wetting agent and starter nutrients and treated withpostemergence applications of a test chemical formulated in anon-phytotoxic solvent mixture which included a surfactant. Plantsranged in height from 2 to 18 cm (1- to 4-leaf stage) for postemergencetreatments. Treated plants and controls were maintained in a greenhousefor 13 to 15 days, after which time all species were compared tocontrols and visually evaluated. Plant response ratings, summarized inTable C, are based on a scale of 0 to 100 where 0 is no effect and 100is complete control. A dash (-) response means no test result.

TABLE C Compound 125 g ai/ha 5 Postemergence Barnyardgrass 10 Blackgrass5 Chickweed 60 Corn 5 Crabgrass, Large 15 Foxtail, Giant 10 Galium 90Johnsongrass 10 Kochia 90 Lambsquarters 60 Morningglory 85 Nutsedge,Yellow 5 Oat, Wild 5 Oilseed Rape 85 Pigweed 85 Ragweed 65 Ryegrass,Italian 5 Soybean 90 Velvetleaf 60 Waterhemp 85 62 g ai/ha 5Postemergence Barnyardgrass 5 Blackgrass 0 Chickweed 55 Corn 5Crabgrass, Large 15 Foxtail, Giant 5 Galium 80 Johnsongrass 5 Kochia 90Lambsquarters 55 Morningglory 65 Nutsedge, Yellow 5 Oat, Wild 0 OilseedRape 60 Pigweed 75 Ragweed 35 Ryegrass, Italian 0 Soybean 40 Velvetleaf70 Waterhemp 75 31 g ai/ha 5 Postemergence Barnyardgrass 0 Blackgrass 0Chickweed 40 Corn 5 Crabgrass, Large 15 Foxtail, Giant 5 Galium 75Johnsongrass 0 Kochia 90 Lambsquarters 70 Morningglory 65 Nutsedge,Yellow 10 Oat, Wild 0 Oilseed Rape 60 Pigweed 75 Ragweed 40 Ryegrass,Italian 5 Soybean 70 Velvetleaf 50 Waterhemp 65 Wheat 5 16 g ai/ha 5Postemergence Barnyardgrass 0 Blackgrass 0 Chickweed 35 Corn 5Crabgrass, Large 10 Foxtail, Giant 0 Galium 35 Johnsongrass 0 Kochia 90Lambsquarters 35 Morningglory 75 Nutsedge, Yellow 0 Oat, Wild 0 OilseedRape 5 Pigweed 65 Ragweed 5 Ryegrass, Italian 0 Soybean 60 Velvetleaf 40Waterhemp 60 Wheat 5

What is claimed is:
 1. A compound selected from Formula 1, N-oxides andsalts thereof,

wherein Q is selected from

Z is O; m is 0 or 1; r is 1; each R¹ is independently halogen, cyano,C₁-C₄ alkyl, C₁-C₄ haloalkyl, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy orSO_(n)R^(1A); n is 0, 1 or 2; R² is halogen or C₁-C₄ alkyl; each R³ isindependently halogen, cyano, C₁-C₄ alkyl, C₂-C₄ alkenyl, C₂-C₄ alkynyl,C₁-C₄ haloalkyl, C₂-C₆ alkylcarbonyl, C₂-C₆ haloalkylcarbonyl, C₂-C₆alkoxycarbonyl, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₂-C₆ alkoxyalkyl orC₂-C₆ haloalkoxyalkyl; and each R^(1A) is independently C₁-C₄ alkyl orC₁-C₄ haloalkyl.
 2. The compound of claim 1 wherein each R¹ isindependently halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl or C₁-C₄ haloalkoxy;R² is halogen or CH₃; and each R³ is independently halogen, cyano, C₁-C₄alkyl or C₁-C₄ haloalkyl.
 3. The compound of claim 1 selected from thegroup consisting of2-[[2-(4-bromo-1H-pyrazol-1-yl)-3-pyridinyl]oxyl]-5-chloropyrimidine,5-chloro-2-[[2-(4-chloro-1H-pyrazol-1-yl)-3-pyridinyl]oxy]pyrimidine,5-chloro-2-[[2-[3-(difluoromethyl)-5-isoxazolyl]-3-pyridinyl]oxy]pyrimidineand5-chloro-2-[[2-[5-(difluoromethyl)-3-isoxazolyl]-3-pyridinyl]oxy]pyrimidine.4. A herbicidal composition comprising a compound of claim 1 and atleast one component selected from the group consisting of surfactants,solid diluents and liquid diluents.
 5. A herbicidal compositioncomprising a compound of claim 1, at least one additional activeingredient selected from the group consisting of other herbicides andherbicide safeners, and at least one component selected from the groupconsisting of surfactants, solid diluents and liquid diluents.
 6. Aherbicidal mixture comprising (a) a compound of claim 1, and (b) atleast one additional active ingredient selected from (b1) photosystem IIinhibitors, (b2) acetohydroxy acid synthase (AHAS) inhibitors, (b3)acetyl-CoA carboxylase (ACCase) inhibitors, (b4) auxin mimics, (b5)5-enol-pyruvylshikimate-3-phosphate (EPSP) synthase inhibitors, (b6)photosystem I electron diverters, (b7) protoporphyrinogen oxidase (PPO)inhibitors, (b8) glutamine synthetase (GS) inhibitors, (b9) very longchain fatty acid (VLCFA) elongase inhibitors, (b10) auxin transportinhibitors, (b11) phytoene desaturase (PDS) inhibitors, (b12)4-hydroxyphenyl-pyruvate dioxygenase (HPPD) inhibitors, (b13)homogentisate solanesyltransferase (HST) inhibitors, (b14) cellulosebiosynthesis inhibitors, (b15) other herbicides including mitoticdisruptors, organic arsenicals, asulam, bromobutide, cinmethylin,cumyluron, dazomet, difenzoquat, dymron, etobenzanid, flurenol,fosamine, fosamine-ammonium, hydantocidin, metam, methyldymron, oleicacid, oxaziclomefone, pelargonic acid and pyributicarb, (b16) herbicidesafeners, and salts of compounds of (b1) through (b16).
 7. A method forcontrolling the growth of undesired vegetation comprising contacting thevegetation or its environment with a herbicidally effective amount of acompound of claim
 1. 8. The compound of claim 1 wherein Q is


9. The compound of claim 8 wherein each R¹ is independently halogen,C₁-C₄ alkyl, C₁-C₄ haloalkyl or C₁-C₄ haloalkoxy; R² is halogen or CH₃;and each R³ is independently halogen, cyano, C₁-C₄ alkyl or C₁-C₄haloalkyl.
 10. The compound of claim 1 that is5-chloro-2-[[2-[5-(difluoromethyl)-3-isoxazolyl]-3-pyridinyl]oxy]pyrimidine.